Diethyl aluminum cyanide → HCID 57254707, compound

HRID 1019015Notes

Reaction equation

HRID 1019015 reaction equation
O1[C@@:18]23[C@:19]4([CH3:28])[C:24](=[CH:25][CH2:26][C@@:2]12[C@H:3]1[C@:15]([CH3:29])([CH2:16][CH2:17]3)[C@@H:6]([C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:5][CH2:4]1)[CH2:23][C@@H:22]([OH:27])[CH2:21][CH2:20]4.[C-]#N.C([Al+]CC)C>ClCCl>[CH3:13][CH:11]([CH2:10][CH2:9][CH2:8][C@H:7]([C@@H:6]1[C@:15]2([CH3:29])[C:3]([C:2]3[CH2:26][CH:25]=[C:24]4[C@:19]([C:18]=3[CH2:17][CH2:16]2)([CH3:28])[CH2:20][CH2:21][C@H:22]([OH:27])[CH2:23]4)=[CH:4][CH2:5]1)[CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 16686413Diethyl aluminum cyanideHCID 57263809HCID 57263809, compound

Product 1

HCID 57254707HCID 57254707, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

8α,9α-Epoxycholest-5-en-3βol (200mg) is dissolved in dichloromethane and the solution is cooled to 0° C. 1.5 ml of a diethylaluminumcyanide-solution (1 M in toluene) is added dropwise. After addition, the reaction mixture is warmed to room temperature and stirred for additional 18 hours. After basic work-up and column chromatography, cholesta-5,8,14-triene-3βol (51 mg) is isolated.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture is warmed to room temperature

Sources & evidence

ORD record
ord-aceef35d7a8046528e7993b0ab1281d2
Source dataset
uspto-grants-2002_11
Patent number
US06486145B2

Reaction notes

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