Water → 1-Hydroxycholest-5-ene

HRID 126671Notes

Reaction equation

HRID 126671 reaction equation
S(O[C@H:12]1[CH2:36][C@H:35]([O:37]C(=O)C)[C@@:34]2([CH3:41])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:42])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.O.[OH-].[Na+]>C1C=CC=CC=1>[OH:37][C@@H:35]1[C@@:34]2([CH3:41])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:42])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:13][CH2:12][CH2:36]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 867375231alpha-Acetoxycholesterol tosylate

Product 1

HCID 1912241-Hydroxycholest-5-ene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 0.900 mg of the tosylate 18 in 50 ml of benzene was stirred and purged with N2. Upon addition of 2.3 ml of Vitride reagent (a solution of 70% Na bis(2-methoxyethoxy aluminum hydride in benzene, Aldrich Chemical Co.), the mixture was refluxed (80°) for 18 hours. The product was isolated in the usual manner: after addition of water and 1.0 ml of 10% NaOH, the inorganic precipitate was removed by filtration and washed with ether, the aqueous phase was further extracted with ether, and the combined organic extracts were washed (10% NaOH), and dried over Na2SO4 and evaporated in vacuo. Chromatography of this residue on silica gel (using 20% ethylacetate in Skellysolve B) gave pure 1α-hydroxycholest-5-ene (19), nmr (CDCl3) δ5.53 (1H, m, C-6), 3.74 (1H, m, C-1); mass spectrum, m/e 386 (M+), 371, 368, 273.

Workup

  1. custompurged with N2
  2. additionUpon addition of 2.3 ml of Vitride reagent (a solution of 70% Na bis(2-methoxyethoxy aluminum hydride in benzene, Aldrich Chemical Co.)
  3. temperaturethe mixture was refluxed (80°) for 18 hours
  4. customThe product was isolated in the usual manner
  5. customthe inorganic precipitate was removed by filtration
  6. washwashed with ether
  7. extractionthe aqueous phase was further extracted with ether
  8. washthe combined organic extracts were washed (10% NaOH)
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-c9abfe8dfa7b4fe2ac75e0cecd424db3
Source dataset
uspto-grants-1981_03
Patent number
USRE030538

Reaction notes

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