Water → HCID 53792303, compound

HRID 1395577Notes

Reaction equation

HRID 1395577 reaction equation
[O:1]=[C:2]1[CH:6]([C:7](=[O:16])[CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([CH3:18])([CH3:17])[C:4]([C:19]#[C:20][C:21]([CH3:25])=[CH:22][CH:23]=[O:24])=[C:3]1[CH3:26].[BH4-].[Na+].O>C(O)C>[O:1]=[C:2]1[CH:6]([C:7](=[O:16])[CH2:8][O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]([CH3:17])([CH3:18])[C:4]([C:19]#[C:20][C:21]([CH3:25])=[CH:22][CH2:23][OH:24])=[C:3]1[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 54161130HCID 54161130, compound

Product 1

HCID 53792303HCID 53792303, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

42 g of 5-[3-oxo-4-phenoxyacetyl-2,5,5-trimethyl-cyclopent-1-en-1-yl]-3-methyl-pent-2-en-4-yn-1-al are dissolved in 420 ml of ethanol. The solution is treated at -40° C. with 1.16 g of sodium borohydride and stirred for 10 minutes. The mixture is then introduced into water and extracted with ether. The 5-[3-oxo-4-phenoxyacetyl-2,5,5-trimethyl-cyclopent-1-en-1-yl]-3-methyl-pent-2-en-4-yn-1-ol is obtained as a viscous oil.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-13d3554082884063abe8414fb02de77a
Source dataset
uspto-grants-1980_05
Patent number
US04204073

Reaction notes

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