Methyl iodide → HCID 69873027, compound

HRID 479319Notes

Reaction equation

HRID 479319 reaction equation
CC([O-])(C)C.[K+].[CH3:7][CH:8]([CH2:10][CH2:11][CH2:12][C@H:13]([C:15]1[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:34])[CH2:25][CH2:26]2)[CH2:21][CH2:20]3)[CH2:17][CH:16]=1)[CH3:14])[CH3:9].IC>CC(O)(C)C.C1COCC1>[CH3:9][CH:8]([CH2:10][CH2:11][CH2:12][C@H:13]([C:15]1[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C:24](=[O:34])[CH2:25][CH2:26]2)=[CH:21][CH2:20]3)[CH2:17][CH:16]=1)[CH3:14])[CH3:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 69873540HCID 69873540, compound

Product 1

HCID 69873027HCID 69873027, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of KOtBu (900 mg, 8.2 mmol) in tBuOH (25 mL) at 45° C. was added cholesta-4,16-dien-3-one (620 mg, 1.6 mmol) in THF (5 mL) and the whole stirred for 20 minutes. Iodomethane (1 ml) was added and the reaction stirred a further 12 hours., concentrated to one half the original volume and poured into 20 mL ice water. Extraction with ethyl acetate, drying over magnesium sulphate and concentration gave a residue which was purified by flash chromatography to give the title compound (220 mg).

Workup

  1. stirringthe reaction stirred a further 12 hours
  2. concentration, concentrated to one half the original volume
  3. additionpoured into 20 mL ice water
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying over magnesium sulphate and concentration
  6. customgave a residue which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-fcc7ed3aae2043f4b748211c479f33df
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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