Hydrogen Peroxide → HCID 69770587, compound

HRID 861808Notes

Reaction equation

HRID 861808 reaction equation
[C:1]([O:9][CH:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[CH:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][CH:17]=4)[C:11]1([CH3:38])[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[OH-:40].[Na+].OO>C1COCC1.C(OCC)C.O>[C:1]([O:9][CH:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[CH:12]([CH2:13][CH2:14][C:15]3[C@H:16]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][CH:17]4[OH:40])[C:11]1([CH3:38])[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 54120485HCID 54120485, compound

Product 1

HCID 69770587HCID 69770587, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2.04 g of 3-benzoyloxy-4,4-dimethylcholesta-8,14-diene (Step A) was dissolved in 50 ml of THF, and 360 ml of 1M borane in THF was added dropwise at 0° C. The mixture was stirred at ambient temperature overnight, cooled to 0° C., and 140 ml of water was added dropwise, followed by 360 ml of 10% sodium hydroxide and 378 ml of 30% hydrogen peroxide. After stirring for 90 mutes, 100 ml of diethyl ether was added to the mixture and the aqueous phase extracted twice with diethyl ether. The combined organic phases were washed twice with sodium bisulphite solution and then with water. After evaporation, the product was purified by chromatography on SiO2 (2% diethyl ether in toluene) to yield 0.62 g of 3-benzoyloxy-4,4-dimethylcholest-8-en-15-ol.

Workup

  1. temperaturecooled to 0° C.
  2. additionwas added to the mixture
  3. extractionthe aqueous phase extracted twice with diethyl ether
  4. washThe combined organic phases were washed twice with sodium bisulphite solution
  5. customAfter evaporation
  6. customthe product was purified by chromatography on SiO2 (2% diethyl ether in toluene)

Sources & evidence

ORD record
ord-4bef146b0f5c473994072438a75473b7
Source dataset
uspto-grants-1998_02
Patent number
US05716777

Reaction notes

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