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 2058140Notes

Reaction equation

HRID 2058140 reaction equation
[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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a8ae85c058c04db295b282d2515d123f
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

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