Triphenylphosphine → HCID 67508166, compound

HRID 1050279Notes

Reaction equation

HRID 1050279 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@H:29]1[CH2:34][C@H:33]2[C@H:35]3[C@H:44]([CH2:45][CH2:46][C@:31]2([CH3:32])[CH2:30]1)[C:43]1[CH:42]=[CH:41][C:40]([O:47][CH3:48])=[CH:39][C:38]=1[CH2:37][CH2:36]3>ClCCl>[Br:1][C@@H:29]1[CH2:34][C@H:33]2[C@H:35]3[C@H:44]([CH2:45][CH2:46][C@:31]2([CH3:32])[CH2:30]1)[C:43]1[CH:42]=[CH:41][C:40]([O:47][CH3:48])=[CH:39][C:38]=1[CH2:37][CH2:36]3

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2275963-Methoxyestra-1(10),2,4-trien-16-ol

Product 1

HCID 67508166HCID 67508166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of 2.67 g (15.0 mmol) N-bromosuccinimide in 18 ml dry dichloromethane, a solution of 3.93 g (15.0 mmol) triphenylphosphine in 18 ml dry dichloromethane is added dropwise at 10° C. After 5 min, 1.72 g (6.0 mmol) 16β-hydroxy-3-methoxy-estra-1,3,5(10)-triene are added and the mixture is stirred at room temperature for 2 h. After column chromatography of the reaction product on silica gel (60 g) using 300 ml of dichloromethane, the target compound is obtained in the form of colorless crystals.

Workup

  1. customthe target compound is obtained in the form of colorless crystals

Sources & evidence

ORD record
ord-13c5dc10842b4a0388704ed3485e495c
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

Loading…