1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Hydroxyprogesterone Impurity 35

HRID 1578024Notes

Reaction equation

HRID 1578024 reaction equation
C(O[C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=O)C.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[C:9]([O:8][CH2:7][C:6](=[O:12])[C:5]1[C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH:13]=1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 10216517,21-Bis(acetyloxy)pregn-4-ene-3,20-dione

Product 1

HCID 15674000Hydroxyprogesterone Impurity 35Yield 83%

Procedure

One gram of 17α,21-diacetoxy-4-pregnene-3,20-dione is heated analogously to Example 1 in "Dowtherm" for 80 minutes to 285° C., worked up, separated, and combined. Recrystallization from hexane/ethyl acetate yields 700 mg of 21-acetoxy-4,16-pregnadiene-3,20-dione (83% of theory), m.p. 146°-148° C.

Workup

  1. customseparated
  2. customRecrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4242d5c10ba5444d8555edf21e1c592d
Source dataset
uspto-grants-1981_09
Patent number
US04290963

Reaction notes

Loading…