1,3-Propanediol → HCID 10951079, compound

HRID 363798Notes

Reaction equation

HRID 363798 reaction equation
[OH:1][C@H:2]1[C@@H:27]2[O:28][C@@H:26]2[C@@:25]2([CH3:29])[C:4](=[CH:5][CH:6]=[C:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[CH2:3]1.[CH2:31]([OH:35])[CH2:32][CH2:33][OH:34].CC(C)([O-])C.[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>O>[OH:34][CH2:33][CH2:32][CH2:31][O:35][C@H:27]1[C@H:26]([OH:28])[C@@:25]2([CH3:29])[C:4](=[CH:5][CH:6]=[C:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[CH2:3][C@H:2]1[OH:1]

Participants

6

Reactant 4

HCID 104421,3-PropanediolHCID 26541Dibenzo-18-crown-6HCID 11004225HCID 11004225, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10951079HCID 10951079, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 21 mg (5.1×10-5 mol) of 3β,25-dihydroxy-1α,2α-epoxy-5,7-cholestadiene, 294 μl (4.1×10-3 mol) of 1,3-propanediol, 19 mg (1.5×10-4 mol) of potassium t-butoxide and 4.8 mg (1.3×10-5 mol) of dibenzo-18-Crown-6 was stirred in an argon atmosphere at 110° C. (bath temperature) for 4 hours. The reaction mixture was poured into water, and the resulting mixture was extracted twice with ethyl acetate and washed once with a saturated aqueous sodium chloride solution. After drying the ethyl acetate layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by fractional thin layer chromatography (silica gel:dichloromethane:ethanol=100:15) to obtain 18 mg (72% yield) of the titled compound as a white powder.

Workup

  1. extractionthe resulting mixture was extracted twice with ethyl acetate
  2. washwashed once with a saturated aqueous sodium chloride solution
  3. dry with materialAfter drying the ethyl acetate layer over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by fractional thin layer chromatography (silica gel:dichloromethane:ethanol=100:15)

Sources & evidence

ORD record
ord-743cb630b7d24e249b3941834145bfe9
Source dataset
uspto-grants-1999_02
Patent number
US05874598

Reaction notes

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