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
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
收藏
页码:1708 / 1717
页数:10
相关论文
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