Ammonium Chloride → HCID 15871128, compound

HRID 1764974Notes

Reaction equation

HRID 1764974 reaction equation
[CH3:1][Li].[CH3:3][CH:4]([CH2:6][CH2:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C:15]3[CH2:16][CH2:17][C:18]4[C@:23]([C:25]=3[CH2:26][CH2:27]2)([CH3:24])[CH2:22][CH2:21][C:20](=[O:30])[CH:19]=4)[CH2:13][CH2:12]1)[CH3:10])[CH3:5].[Cl-].[NH4+]>C(OCC)C>[CH3:1][C@@:18]12[CH2:19][C:20](=[O:30])[CH2:21][CH2:22][C@:23]1([CH3:24])[C:25]1[CH2:26][CH2:27][C@@:28]3([CH3:29])[C@@H:14]([CH2:13][CH2:12][C@@H:11]3[C@H:9]([CH3:10])[CH2:8][CH2:7][CH2:6][CH:4]([CH3:3])[CH3:5])[C:15]=1[CH2:16][CH2:17]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15871124HCID 15871124, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 15871128HCID 15871128, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.85 ml of a methyllithium solution (1.6 N, in diethyl ether) are added to a suspension of 130 mg cuprous iodide in diethyl ether at 0° C. The resulting mixture is stirred for one hour before a solution of 130 mg cholesta-4,8-dien-3-one in 1 ml diethyl ether is added. After being stirred for 30 minutes the reaction mixture is poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer is separated, washed with brine, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with mixture of hexane and ethyl acetate to give 80 mg 5-methyl-5β-cholest-8-en-3-one as a white solid.

Workup

  1. additionis added
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customAfter evaporation of the solvent the residue
  8. customis chromatographed with mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-124c5be7e4dc4399850db782aa27946b
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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