1,3-Propanediol → HCID 15850430, compound

HRID 363799Notes

Reaction equation

HRID 363799 reaction equation
[O:1]1[C@H:3]2[C@H:4]([OH:29])[CH2:5][C:6]3[C@:26]([CH3:27])([C@@H:2]12)[C@@H:25]1[C:9]([C@H:10]2[C@:22]([CH3:28])([CH2:23][CH2:24]1)[C@@H:13]([C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:11]2)=[CH:8][CH:7]=3.[CH2:30]([OH:34])[CH2:31][CH2:32][OH:33].CC(C)([O-])C.[K+]>O>[OH:33][CH2:32][CH2:31][CH2:30][O:34][C@H:3]1[C@H:2]([OH:1])[C@@:26]2([CH3:27])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5][C@H:4]1[OH:29]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 15666815HCID 15666815, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15850430HCID 15850430, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 275 mg (6.9×10-4 mol) of 1α,2α-epoxy-3β-hydroxy-5,7-cholestadiene, 4 ml (5.5×10-2 mol) of 1,3-propanediol, and 258 mg (2.1×10-3 mol) of potassium t-butoxide was stirred in an argon atmosphere at 110° C. (bath temperature) for 4.5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted twice with diethyl ether and washed three times with water. Sodium chloride was added to the aqueous layer, and the mixture was extracted twice with ethyl acetate and washed once with a saturated aqueous sodium chloride solution. After drying the combined organic layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by flash column chromatography (silica gel:dichloro-methane:ethanol=10:1) to obtain 229 mg (70% yield) of the titled compound as a white powder.

Workup

  1. extractionthe resulting mixture was extracted twice with diethyl ether
  2. washwashed three times with water
  3. additionSodium chloride was added to the aqueous layer
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washwashed once with a saturated aqueous sodium chloride solution
  6. dry with materialAfter drying the combined organic layer over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by flash column chromatography (silica gel:dichloro-methane:ethanol=10:1)

Sources & evidence

ORD record
ord-b3cf8c1b3c884106b8f6f9211deac89d
Source dataset
uspto-grants-1999_02
Patent number
US05874598

Reaction notes

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