Acetic Acid → HCID 70565475, compound

HRID 126670Notes

Reaction equation

HRID 126670 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C(O)(=O)C.O[C@@H:10]1[C@@:34]2([CH3:35])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[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][C@@H:12]([OH:37])[CH2:11]1.[OH-].[K+].C(O)(=O)C.O>C(OCC)C.CO>[C:1]([O:4][C@@H:10]1[C@@:34]2([CH3:35])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[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][C@@H:12]([OH:37])[CH2:11]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 86737522HCID 86737522, compound

Product 1

HCID 70565475HCID 70565475, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 600 mg of 1α-hydroxycholesterol diacetate (16) in 1.6 ml of diethyl ether was cooled to ice-bath temperature and 1.6 ml of 0.1 N KOH in methanol was added slowly with stirring. After stirring for 2.5 hours, acetic acid (0.25 ml) and water was added, the mixture was extracted with ether (3×), combined extracts were dried (Na2SO4) and evaporated to dryness to give 0.55 g of 1α-acetoxycholesterol (17), homogeneous on tlc. nmr (CDCl3) δ5.55 (1H, broad, C-6), 5.00 (1H, m, C-1), 3.62 (1H, m, C-3), 2.10 (3H, s, OAc).

Workup

  1. additionwas added slowly
  2. stirringAfter stirring for 2.5 hours
  3. extractionthe mixture was extracted with ether (3×)
  4. dry with materialwere dried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-97c691727a954e0a8b007c3fcd9db61e
Source dataset
uspto-grants-1981_03
Patent number
USRE030538

Reaction notes

Loading…