Bicarbonate Ion → 7alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

HRID 650351Notes

Reaction equation

HRID 650351 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].C(Cl)(Cl)(Cl)[Cl:51]>C(#N)C.ClCCl>[Cl:51][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 158381567a-(5-Hydroxypentyl)-estr-4-ene-3,17-dione

Product 1

HCID 571565697alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The same product is obtained from 8.05 g of 7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione (Example 1b) by a 3.5-hour reaction with 8.66 g of triphenylphosphine in 85 ml of carbon tetrachloride and 30 ml of acetonitrile at room temperature. The reaction mixture is diluted with dichloromethane, shaken out with saturated bicarbonate solution and with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with dichloromethane and ethyl acetate, whereby 4.08 g of 7α-(5-chloropentyl)-estr-4-ene-3,17-dione is obtained, [α]D22=+68° (c=0.5% in chloroform)

Workup

  1. dry with materialdried with sodium sulfate
  2. concentrationconcentrated by evaporation in a vacuum
  3. customThe residue is chromatographed on silica gel with dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-d9d4c0ebe4714f68a5b8671f9b93a85f
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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