Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 415699

反応式

HRID 415699 の反応式
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=O)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:22]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-

生成物 1

HCID 10732902(S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate収率 111.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixed solution comprising (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid tert-butyl ester (11.7 g), (carboethoxymethylene)triphenylphosphorane (20.7 g) and toluene (100 ml) was heated with stirring at 100° C. for 18 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=8:1), to obtain the title compound (17 g).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=8:1)

出典と根拠

ORDレコード
ord-981112ebcf974b618030a67fa482d260
出典データセット
uspto-grants-2012_01
特許番号
US08088796B2

関連ノート

読み込み中…