Methanol → 21-Butyryl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973717Notes

Reaction equation

HRID 1973717 reaction equation
[C:1](OCC)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:9][C@@H:10]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:26]2[C:25](=[O:31])[CH2:24][C@@:23]2([CH3:32])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=[O:22])[CH3:21])[CH2:11]1.[H-].[Na+].CO>CS(C)=O>[C:1]([CH2:21][C:20](=[O:22])[C@@H:19]1[C@:23]2([CH3:32])[C@H:16]([C@H:15]3[C@H:26]([C:25](=[O:31])[CH2:24]2)[C@:27]2([CH3:30])[C@H:12]([CH2:11][C@H:10]([OH:9])[CH2:29][CH2:28]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 7762Ethyl butyrateHCID 24758Sodium hydrideHCID 104845Alphaxalone

Product 1

HCID 8673428421-Butyryl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl butyrate (0.84 ml) was added to a mixture of 3α-hydroxy-5α-pregnane-11,20-dione (665 mg) and sodium hydride (150 mg.) in dry dimethyl sulphoxide (10 ml.). The mixture was stirred, under N2, for 13/4 hrs. The reaction mixture was treated with methyl alcohol to destroy excess sodium hydride, then poured into 2N-hydrochloric acid. The product was extracted with ethyl acetate and the combined extracts were washed with water, dried and evaporated. Preparative t.l.c. of the residue (859 mg.) gave two fractions. The more polar fraction was title compound (244 mg.) [α]D + 74.0°, λmax. 278 nm (ε 12,980).

Workup

  1. customto destroy excess sodium hydride
  2. additionpoured into 2N-hydrochloric acid
  3. extractionThe product was extracted with ethyl acetate
  4. washthe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customof the residue (859 mg.) gave two fractions

Sources & evidence

ORD record
ord-04599ae8fc9c42da9ae36406e75c1e56
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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