Dichloromethane → 4-Cyanophenylethyl cyclopropyl carbinol

HRID 2165378Notes

Reaction equation

HRID 2165378 reaction equation
[CH:1]1([C:4]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[O:5])[CH2:3][CH2:2]1.[BH4-].[BH4-].[Na+].C(Cl)Cl>C(O)C.O>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH:4]([CH:1]2[CH2:3][CH2:2]2)[OH:5])=[CH:9][CH:10]=1)#[N:15]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 13316970HCID 13316970, compound

Product 1

HCID 133169714-Cyanophenylethyl cyclopropyl carbinolYield 99.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 30.9 g of 4-cyanophenylethyl cyclopropyl ketone in 90 ml of absolute ethanol was added 1.48 g of soldium borohydride, and the mixture was stirred at room temperature for three hours. The product isolated from the reaction still contained unreacted starting material, so the material was redissolved in 90 ml of ethanol and treated with 0.7 g additional sodium borohydride for three hours. The product obtained by evaporation of the solvent, trituration of the residue with methylene dichloride and water, and isolation of the product from the organic phase, gave 31.0 g of 4-cyanophenylethyl cyclopropyl carbinol as an oil which crystallized to a colorless solid, m.p. 70°-71° C.

Workup

  1. customThe product isolated from the reaction still contained unreacted

Sources & evidence

ORD record
ord-edfbe1af0286485e98f31e326409ee19
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

Loading…