Carbon Tetrachloride → HCID 70506676, compound

HRID 2418146Notes

Reaction equation

HRID 2418146 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:9]2[C@H:8]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH3:7])[C@:20]1([CH3:21])[C:15]([CH2:16][C@@H:17]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19]1)=[CH:14][CH2:13]3)(=[O:3])[CH3:2].C(Cl)(Cl)(Cl)Cl.C([OH:43])(C)(C)C.C(OC(=O)C)(=O)C>C(Cl)Cl.[O-2].[Cr+6].[O-2].[O-2].C(O)(=O)C>[C:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:9]2[C@H:8]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH3:7])[C@:20]1([CH3:21])[C:15]([CH2:16][C@@H:17]([O:25][C:26](=[O:33])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:18][CH2:19]1)=[CH:14][C:13]3=[O:43])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 5943Carbon Tetrachloride2×HCID 6386tert-ButanolHCID 7918Acetic AnhydrideHCID 70506227HCID 70506227, compound

Product 1

HCID 70506676HCID 70506676, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

6.9 g of 17β-acetoxy-3β-benzoyloxy-15β,16β-methylene-5-androstene was combined with 69 ml of carbon tetrachloride with an acetic tert.-butyl chromate solution prepared from 10.35 g of chromium(VI) oxide, 90 ml of carbon tetrachloride, 28.2 ml of tert.-butyl alcohol, 37.2 ml of acetic acid, and 134 ml of acetic anhydride. The reaction solution was then stirred for 32 hours at 80° C., diluted with methylene chloride, and washed with sodium acetate solution, sodium bicarbonate solution, and water. After drying and evaporation, the resultant residue was chromatographed on silica gel, thus obtaining 4.4 g of 17β-acetoxy-3β-benzoyloxy-15β,16β-methylene-5-androsten-7-one, mp 245°-246° C. (acetone-diisopropyl ether).

Workup

  1. washwashed with sodium acetate solution, sodium bicarbonate solution, and water
  2. customAfter drying
  3. customevaporation
  4. customthe resultant residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-cd085c4e035947eda07ced365db03437
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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