Acetic Acid → HCID 22212670, compound

HRID 1606491Notes

Reaction equation

HRID 1606491 reaction equation
C1CO[C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[O:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:25])[CH2:15][CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:2]1.C(O)(=O)C>C(Cl)(Cl)Cl>[OH:25][C@@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[C@H:20]([OH:24])[CH2:21][C@@:22]2([CH3:23])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[C:3](=[O:2])[CH3:4])[CH2:13]1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 86733334HCID 86733334, compound

Product 1

HCID 22212670HCID 22212670, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 20,20-ethylenedioxy-3α-hydroxy-5α-pregnan-11-one (350 mg.) in mthanol (20 ml.) was treated with 25% aqueous acetic acid (2 ml.) at room temperature. After 18 hr. more 25 % aqueous acetic acid (2 ml.) was added and after a further 27 hr. the mixture was diluted with chloroform, washed with water, dried (Na2SO4) and evaporated to leave a white foam (300 mg.). Crystallisation from acetone and petroleum ether (b.p. 60°-80°) gave the title compound (160 mg.) as off-white rods; m.p. 152°-154°; [α]D + 79°.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto leave a white foam (300 mg.)
  5. customCrystallisation from acetone and petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-434086f0b34a4d4c8b58f756d3cb00ea
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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