Methanol → HCID 86584300, compound

HRID 479322Notes

Reaction equation

HRID 479322 reaction equation
[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH2:17][CH:18]=[C:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]1([CH3:38])[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:47])C=1.[OH-].[Na+].CO>ClCCl>[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH:17]3[O:47][C@H:18]3[C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]1([CH3:38])[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69873486HCID 69873486, compound

Product 1

HCID 86584300HCID 86584300, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3β-benzoyloxy-4,4dimethylcholesta-5,16-diene (250 mg, 4.8 mmol) in dichloromethane (5 mL) at ice bath temperature was added mCPBA (180 mg, 5.2 mmol) and the whole stirred for 3 hours. 2N NaOH (5 mL) was added and the aqueous phase extracted with dichloromethane. Concentration under reduced pressure gave a residue which was tritured with methanol and purified by flash chromatography to give 3β-benzoyloxy-4,4-dimethyl-16α-epoxycholesta-5-ene (50 mg).

Workup

  1. extractionthe aqueous phase extracted with dichloromethane
  2. concentrationConcentration under reduced pressure
  3. customgave a residue which
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b71f69e1610341e2a6d3e0398c5c86fe
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

Loading…