Sodium Hydroxide → HCID 15871125, compound

HRID 1816503Notes

Reaction equation

HRID 1816503 reaction equation
[C-:1]#[N:2].C([Al+]CC)C.[CH3:8][CH:9]([CH2:11][CH2:12][CH2:13][C@H:14]([C@@H:16]1[C@:33]2([CH3:34])[C@H:19]([C:20]3[CH2:21][CH2:22][C:23]4[C@:28]([C:30]=3[CH2:31][CH2:32]2)([CH3:29])[CH2:27][CH2:26][C:25](=[O:35])[CH:24]=4)[CH2:18][CH2:17]1)[CH3:15])[CH3:10].[OH-].[Na+]>O1CCCC1>[C:1]([C@@:23]12[CH2:24][C:25](=[O:35])[CH2:26][CH2:27][C@:28]1([CH3:29])[C:30]1[CH2:31][CH2:32][C@@:33]3([CH3:34])[C@@H:19]([CH2:18][CH2:17][C@@H:16]3[C@H:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:9]([CH3:8])[CH3:10])[C:20]=1[CH2:21][CH2:22]2)#[N:2].[C:1]([C@:23]12[CH2:24][C:25](=[O:35])[CH2:26][CH2:27][C@:28]1([CH3:29])[C:30]1[CH2:31][CH2:32][C@@:33]3([CH3:34])[C@@H:19]([CH2:18][CH2:17][C@@H:16]3[C@H:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:9]([CH3:8])[CH3:10])[C:20]=1[CH2:21][CH2:22]2)#[N:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15871124HCID 15871124, compoundHCID 16686413Diethyl aluminum cyanide

Product 2

HCID 15871125HCID 15871125, compoundHCID 15871126HCID 15871126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 ml of a diethylaluminum cyanide solution (1 N, in toluene) are added to a solution of 3.82 g cholesta-4,8-dien-3-one in 60 ml tetrahydrofuran at 0° C. The reaction mixture is warmed to room temperature and stirred for 4 hours. 20 ml of a sodium hydroxide solution (1 N) are added before the mixture is extracted with diethyl ether. The organic layer is separated, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with a mixture of hexane and ethyl acetate to give 1.46 g 5-cyano-5β-cholest-8-en-3-one and 1.76 g 5-cyano-5α-cholest-8-en-3-one as pale yellow crystals.

Workup

  1. extractionis extracted with diethyl ether
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customAfter evaporation of the solvent the residue
  6. customis chromatographed with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-005611731d174c08985c74604152bfdc
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

Loading…