Lithium hydride → (1RS,4SR,5RS)-4-(4,8-dimethyl-5-oxo-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

HRID 2058140ノート

反応式

HRID 2058140 の反応式
[C:1]([CH:4]([CH3:20])[CH2:5][CH2:6][CH2:7][C:8]1([CH3:19])[CH:14]2[O:15][C:11]([CH2:16][CH2:17][OH:18])([CH2:12][CH2:13]2)[CH2:10][O:9]1)([OH:3])=O.[H-].[Li+].[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26][Li].C(=O)(O)[O-].[Na+]>CCOCC>[CH3:20][CH:4]([C:1](=[O:3])[CH2:26][CH:25]=[C:24]([CH3:28])[CH3:23])[CH2:5][CH2:6][CH2:7][C:8]1([CH3:19])[CH:14]2[O:15][C:11]([CH2:16][CH2:17][OH:18])([CH2:12][CH2:13]2)[CH2:10][O:9]1

参加物

6

反応物 4

HCID 62714Lithium hydrideHCID 516892Sodium BicarbonateHCID 23349564(1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanolHCID 178506861C5H9Li

生成物 1

HCID 13367193(1RS,4SR,5RS)-4-(4,8-dimethyl-5-oxo-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A mixture of (1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (58 mg, 0.2 mM), lithium hydride (10 mg, 1.25 mM) and ether (5 ml) is stirred at room temperature under nitrogen for two hours. An excess of 3-methyl-2-butenyl lithium is added to this mixture at room temperature. The resulting mixture is stirred for two hours and then treated with 5% sodium bicarbonate solution (5 ml) and extracted with ethyl acetate (3×20 ml). The combined organic layers are dried (Na2SO4), evaporated in vacuo and the residue is purified by column chromatography on silica gel (7 g) with ether to give (1RS,4SR,5RS)-4-(4,8-dimethyl-5-oxo-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (13 mg), 25%) as a colorless oil).

後処理

  1. stirringThe resulting mixture is stirred for two hours
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. customevaporated in vacuo
  5. customthe residue is purified by column chromatography on silica gel (7 g) with ether

出典と根拠

ORDレコード
ord-a8ae85c058c04db295b282d2515d123f
出典データセット
uspto-grants-1980_07
特許番号
US04215048

反応ノート

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