Pyridine → 1-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerol

HRID 843569ノート

反応式

HRID 843569 の反応式
[Si:1]([O:8][CH2:9][CH:10]([CH2:13][OH:14])[O:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].N1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 1049PyridineHCID 5364783Oleoyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

生成物 1

HCID 877595431-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerol収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of alcohol 15 (1.1 g, 5.0 mmol) in CH2Cl2 (10 mL) was added oleoyl chloride (1.8 mL, 5.5 mmol) followed, after 5 min, by the addition of pyridine (0.44 mL, 5.5 mmol). After TLC analysis indicated that the reaction had gone to completion, the mixture was partitioned between ethyl acetate (100 mL) and H2O (30 mL), the organic extract was dried (MgSO4) and concentrated to give 1-O-t-butyldimethylsilyl-2-O-methyl-3-O-oleoyl-rac-glycerol (16) (2.4 g, 99%) as a dark brown oil.

後処理

  1. customthe mixture was partitioned between ethyl acetate (100 mL) and H2O (30 mL)
  2. extractionthe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-29690b9f588348f9bcabca01aec8809a
出典データセット
uspto-grants-2002_04
特許番号
US06380177B1

反応ノート

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