Water → 4-Cyanophenylethyl cyclopropyl carbinol

HRID 544622Notes

Reaction equation

HRID 544622 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-].[Na+].C(Cl)Cl.O>C(O)C>[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

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydride2×HCID 13316970HCID 13316970, compound

Product 1

HCID 133169714-Cyanophenylethyl cyclopropyl carbinolYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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 sodium 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-675197aaecaa49c4a4d2dca8a72e0cd7
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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