Water → HCID 86733294, compound

HRID 1606352Notes

Reaction equation

HRID 1606352 reaction equation
ClCC([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:30][C@@:29]2([CH3:31])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:28]2[C:27](=[O:32])[CH2:26][C@@:25]2([CH3:33])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C:22](=[O:24])[CH3:23])[CH2:13][C@@H:12]1[OH:34])=O.Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+].O>CO>[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:30][C@@:29]2([CH3:31])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:28]2[C:27](=[O:32])[CH2:26][C@@:25]2([CH3:33])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C:22](=[O:24])[CH3:23])[CH2:13][C@@H:12]1[OH:34]

Participants

6

Reactant 4

HCID 962WaterHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 22789163HCID 22789163, compound

Product 1

HCID 86733294HCID 86733294, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2β-(4'-Chloroacetoxy-n-butoxy)-3α-hydroxy-5α-pregnane-11,20-dione (380 mg.) was dissolved in methanol (40 ml.) and the stirred solution heated to 50°C. Perchloric acid (0.5 ml.) was added and the mixture stirred at 50°C for 5 hours. The mixture was neutralised with sodium bicarbonate solution, poured into water and extracted with ether (2 × 100 ml.). The combined extracts were washed with water (200 ml.), dried over anhydrous sodium sulphate and evaporated in vacuo to a white foam (270 mg.) which was purified by preparative tlc in acetone/petroleum ether 1/1 to give the title compound (170 mg.) [α]D + 79.5°

Workup

  1. extractionextracted with ether (2 × 100 ml.)
  2. washThe combined extracts were washed with water (200 ml.)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated in vacuo to a white foam (270 mg.) which
  5. customwas purified by preparative tlc in acetone/petroleum ether 1/1

Sources & evidence

ORD record
ord-f4c5b7584c7e4d67ac8c26938a715155
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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