Sodium hydride → Benzyl (2e,4s)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-7-methyl-2-octenoate

HRID 1796862ノート

反応式

HRID 1796862 の反応式
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:13]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(OP([CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])(OCC)=O)C.[H-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])/[CH:13]=[CH:28]/[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 281239Benzyl (diethoxyphosphoryl)acetateHCID 87901094(2s)-2-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-5-methylhexanal

生成物 1

HCID 131725709Benzyl (2e,4s)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-7-methyl-2-octenoate

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of Example 8H (2.61 g, 9.16 mmol), benzyl diethylphosphonoacetate (2.83 g, 9.90 mmol), and sodium hydride (0.24 g, 10 mmol) in benzene (40 mL) at room temperature was stirred 2 hours, diluted with ethyl acetate, washed sequentially with saturated aqueous NH4Cl and pH 7 buffer, dried (MgSO4), filtered, and concentrated. Flash column chromatography (silica gel, 2:1 hexanes/CH2Cl2) provided the desired product. MS (ESI) m/e 419 (M+H)+.

後処理

  1. washwashed sequentially with saturated aqueous NH4Cl and pH 7 buffer
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-25c8fb8e2b6d4169a6a94993c662f51b
出典データセット
uspto-grants-2006_04
特許番号
US07030262B2

反応ノート

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