Carbon Tetrachloride → HCID 88717769, compound

HRID 2418141Notes

Reaction equation

HRID 2418141 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@:7]3([O:30][C@@H:8]3[C@H:9](O)[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:28][C@@H:13]3[C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6]1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:51]>N1C=CC=CC=1.C(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@:7]3([O:30][C@@H:8]3[C@@H:9]([Cl:51])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:28][C@@H:13]3[C:14]32[O:27][CH2:26][CH2:25][O:24]3)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 88717391HCID 88717391, compound

Product 1

HCID 88717769HCID 88717769, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 24 g of 3β-acetoxy-5,6β-epoxy-17,17-ethylenedioxy-15β,16β-methylene-5β-androstan-7β-ol in 48 ml of pyridine and 48 ml of carbon tetrachloride was combined with 28 g of triphenylphosphine and stirred for 1.5 hours at room temperature. The reaction mixture was diluted with methylene chloride, washed with water, dried, and evaporated. The residue was chromatographed on silica gel, thus producing 21.5 g of 3β-acetoxy-7α-chloro-5,6β-epoxy-17,17-ethylenedioxy-15β,16β-methylene-5β-androstane, mp 169°-170° C. (diisopropyl ether).

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-05c36a6523a3437297f1b09dbac82f02
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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