Carbon Tetrachloride → HCID 69916333, compound

HRID 1837274Notes

Reaction equation

HRID 1837274 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][C@H:14]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]O)=[CH:11][C:10](=[O:34])[CH2:9][CH2:8]1)(=[O:3])[CH3:2].[Cl:35]C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C(Cl)Cl>[C:1]([O:4][C@@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][C@H:14]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][Cl:35])=[CH:11][C:10](=[O:34])[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 69916490HCID 69916490, compound

Product 1

HCID 69916333HCID 69916333, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

15.8 g of 11α-acetoxy-7α-(9-hydroxynonyl)-estr-4-ene-3,17-dione is reacted in 65 ml of acetonitrile with 184 ml of tetrachloromethane and 17.9 g of triphenylphosphine at room temperature. After 5 hours, it is diluted with methylene chloride, washed neutral with saturated sodium bicarbonate solution and water and dried. The crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient. Yield: 7.8 g of 11α-acetoxy-7α-(9-chlorononyl)-estr-4-ene-3,17-dione with a melting point of 113-115° C.

Workup

  1. washwashed neutral with saturated sodium bicarbonate solution and water
  2. customdried
  3. customThe crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-293499c46df840be8da095bc1fdc93ec
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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