Sodium borohydride → HCID 178444482, compound

HRID 1109695Notes

Reaction equation

HRID 1109695 reaction equation
[C:1]([C:3](=[C:9]1[CH2:14][CH2:13][CH:12](/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[BH4-].[Na+]>C(O)C.O>[C:1]([CH:3]([C@H:9]1[CH2:14][CH2:13][C@H:12](/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19019238ethyl cyano-[4-(1E-pentenyl)cyclohexylidene]acetate

Product 1

HCID 178444482HCID 178444482, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 46.0 g of ethyl cyano-[4-(1E-pentenyl)cyclohexylidene]acetate in 120 ml of ethanol is added dropwise at 5°-10° C. within 40 minutes to a mixture of 6.7 g of sodium borohydride and 120 ml of ethanol. The reaction mixture is stirred at 5° C. for 45 minutes, then diluted with 750 ml of water and extracted with three 250 ml portions of diethyl ether. The extract is washed neutral with water, dried over sodium sulphate and concentrated. There is obtained crude ethyl cyano-[trans-4-(1E-pentenyl)cyclohexyl]acetate (cis content <20%).

Workup

  1. extractionextracted with three 250 ml portions of diethyl ether
  2. washThe extract is washed neutral with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cbbe6e6ddc504fa3aac856bb6bd8c708
Source dataset
uspto-grants-1994_06
Patent number
US05322638

Reaction notes

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