Dimethyl Sulfoxide → 3-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

HRID 497006ノート

反応式

HRID 497006 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][CH2:19][CH:20]([CH2:23][OH:24])[O:21][CH3:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:18][CH2:19][CH:20]([O:21][CH3:22])[CH:23]=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

生成物 1

HCID 543075043-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Oleyl 2-O-methyl-rac-glycerate (Compound 76) To a solution of oxalyl chloride (87 (L, 1.0 mmol) in CH2Cl2 (7 mL) at −78° C. was added DMSO (71 (L, 1.0 mmol). After 20 min, alcohol Compound 42 (0.20 g, 0.91 mmol) was added followed, after another 20 min, by the addition of triethylamine (0.63 mL, 4.6 mmol). The reaction was warmed to room temperature over a 10 min period, filtered through a plug of silica-gel, which was washed with ethyl acetate (50 mL) and concentrated to give 3-O-t-butyldimethylsilyl-2-O-methyl-rac-glyceraldehyde Compound 73 (0.20 g, 100%) as a colourless oil.

後処理

  1. filtrationfiltered through a plug of silica-gel, which
  2. washwas washed with ethyl acetate (50 mL)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-7e2d0504d2a146d8ae2b7e08bfca9af3
出典データセット
uspto-grants-2005_09
特許番号
US06949528B1

反応ノート

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