Acetic Acid → HCID 21312640, compound

HRID 971931Notes

Reaction equation

HRID 971931 reaction equation
[BH4-].[Na+].C(O)C.[O:6]=[C:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])/[CH:8]=[CH:9]/[CH:10]1[CH2:12][C:11]1([C:17]([O:19][CH3:20])=[O:18])[C:13]([O:15][CH3:16])=[O:14].C(O)(=O)C>O>[OH:6][CH:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])/[CH:8]=[CH:9]/[CH:10]1[CH2:12][C:11]1([C:13]([O:15][CH3:16])=[O:14])[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 21312609HCID 21312609, compound

Product 1

HCID 21312640HCID 21312640, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.5 g of sodium borohydride in 50 ml. of 95% ethanol is added to a solution of the compound of formula VI, dimethyl trans-2-(3-oxo-1-octenyl)cyclopropane-1,1-dicarboxylate (35 g), described in Example 2. After 15 min. at room temperature the mixture is cooled in ice and rendered neutral by the addition of acetic acid. Water is added and the mixture extracted with ethyl-acetate. The extract was dried (Na2SO4) and the evaporated. The residue is purified by chromatography on silica gel to afford the title compound, nmr (CDCl3) δ 0.90 (t, 3H), 2.33 (1H), 3.73 (s, 3H) 4.05 (m, 1H).

Workup

  1. extractionthe mixture extracted with ethyl-acetate
  2. dry with materialThe extract was dried (Na2SO4)
  3. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ee9e4eb765d54328a3648b858bc01a95
Source dataset
uspto-grants-1979_07
Patent number
US04161608

Reaction notes

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