One-Pot Etherification of Ketones and Aldehydes with Organic Halides Using Sodium Hydride as a Reductant

被引：2

作者：

Meng, Qingwei ^{[1
]}

Gong, Bin ^{[1
]}

Hui, Chuang ^{[1
]}

Gao, Zhanxian ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116011, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 10期

关键词：

Aldehyde; etherification; ketone; one pot; sodium hydride; CARBONYL-COMPOUNDS; UNSYMMETRICAL ETHERS; IRON(III) CHLORIDE; EFFICIENT; TRIETHYLSILANE; ACID;

D O I：

10.1080/00397910802579178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot etherification reaction of aromatic and some aliphatic carbonyl compounds with organic halides in the presence of sodium hydride as a reducing reagent proceeded smoothly in dioxane, a polar solvent with higher boiling point, to provide desired ethers in moderate to high yields.

引用

页码：1708 / 1717

页数：10

共 12 条

[1] Use of CaH2 as a reductive hydride source:: reduction of ketones and imines with CaH2/ZnX2 in the presence of a Lewis acid [J].

Aida, T ;

Kuboki, N ;

Kato, K ;

Uchikawa, W ;

Matsuno, C ;

Okamoto, S .

TETRAHEDRON LETTERS, 2005, 46 (10) :1667-1669

[2] Reductive etherification of carbonyl compounds with alkyl trimethylsilylethers using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3 [J].

Chandrasekhar, S ;

Chandrashekar, G ;

Babu, BN ;

Vijeender, K ;

Reddy, KV .

TETRAHEDRON LETTERS, 2004, 45 (28) :5497-5499

[3]

HARTZ N, 1992, SYNLETT, P569

[4] EFFICIENT REDUCTIVE ETHERIFICATION OF CARBONYL-COMPOUNDS WITH ALKOXYTRIMETHYLSILANES [J].

HATAKEYAMA, S ;

MORI, H ;

KITANO, K ;

YAMADA, H ;

NISHIZAWA, M .

TETRAHEDRON LETTERS, 1994, 35 (25) :4367-4370

[5] An efficient and convenient method for the direct conversion of alkyl silyl ethers into the corresponding alkyl ethers catalyzed by iron(III) chloride [J].

Iwanami, K ;

Yano, K ;

Oriyama, T .

SYNTHESIS-STUTTGART, 2005, (16) :2669-2672

[6] A highly efficient method for the reductive etherification of carbonyl compounds with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride [J].

Iwanami, K ;

Seo, H ;

Tobita, Y ;

Oriyama, T .

SYNTHESIS-STUTTGART, 2005, (02) :183-186

[7] A NOVEL METHOD FOR THE PREPARATION OF SYMMETRICAL AND UNSYMMETRICAL ETHERS - TRITYL PERCHLORATE PROMOTED REDUCTION OF CARBONYL-COMPOUNDS WITH TRIETHYLSILANE [J].

KATO, J ;

IWASAWA, N ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1985, (06) :743-746

[8] Bismuth bromide-catalyzed reductive coupling of carbonyl compounds and its application to the synthesis of novel crownophanes [J].

Komatsu, N ;

Ishida, J ;

Suzuki, H .

TETRAHEDRON LETTERS, 1997, 38 (41) :7219-7222

[9] Reductive etherification of aromatic aldehydes with decaborane [J].

Lee, SH ;

Park, YJ ;

Yoon, CM .

TETRAHEDRON LETTERS, 1999, 40 (33) :6049-6050

[10] SYNTHETIC METHODS AND REACTIONS .130. GENERAL ETHER SYNTHESIS UNDER MILD ACID-FREE CONDITIONS - TRIMETHYLSILYL IODIDE CATALYZED REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS WITH TRIALKYLSILANES TO SYMMETRICAL ETHERS AND REDUCTIVE CONDENSATION WITH ALKOXYSILANES TO UNSYMMETRICAL ETHERS [J].

SASSAMAN, MB ;

KOTIAN, KD ;

PRAKASH, GKS ;

OLAH, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4314-4319

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