Pyridine → HCID 86587008, compound

HRID 861809Notes

Reaction equation

HRID 861809 reaction equation
C[C:2]1(C)C(O)C[CH2:24][C@@:23]2(C)[CH:3]1CC[C:6]1[C:7]3[C@:19]([CH3:29])([CH2:20][CH2:21][C:22]=12)[C@@H:10]([C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9][CH:8]=3.[C:31]([O:34][C:35](=[O:37])[CH3:36])(=O)[CH3:32].N1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[C:35]([O:34][CH:31]1[CH2:2][CH2:3][C@@:23]2([CH3:24])[CH:39]([CH2:40][CH2:41][C@:42]3([CH3:43])[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:29])[C@@:7]3([CH3:6])[CH2:8][CH2:9][C@@H:10]2[C@H:11]([CH3:18])[CH2:12][CH:13]=[CH:14][C:15]([CH3:17])=[CH2:16])[CH2:32]1)(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21124658HCID 21124658, compound

Product 1

HCID 86587008HCID 86587008, compound

Procedure

1.3 g of 4,4-dimethylcholesta-8,14-diene-3-ol (Schroepfer et al., Chemistry and Physics of Lipids 47, p. 187 (1988)) were dissolved in 7.5 ml of pyridine and 7.5 ml of acetic anhydride and stirred at 22° C. overnight. The mixture was evaporated in vacuo, stripped twice with toluene, and purified by flash chromatography on SiO2 (toluene). The first 300 ml of eluate was evaporated, and the product crystallized from diethyl ether to yield 140 mg of 3-acetoxy-8,14-dimethylcholestadiene. Melting point: 120°-125° C. (with destruction). MS (molecular ion): 454.4.

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompurified by flash chromatography on SiO2 (toluene)
  3. customThe first 300 ml of eluate was evaporated
  4. customthe product crystallized from diethyl ether

Sources & evidence

ORD record
ord-271a4ae21fb54a59b8b4e285c88f75a2
Source dataset
uspto-grants-1998_02
Patent number
US05716777

Reaction notes

Loading…