5-bromopentyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate → 5-bromopentyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate

HRID 1269358Notes

Reaction equation

HRID 1269358 reaction equation
[C:1](=[O:38])([O:9][CH2:10]/[C:11](/[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1)=[C:12](/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)\[CH2:13][O:14][Si](C(C)(C)C)(C)C)[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8]>CC#N.C1(C)C=CC=CC=1>[C:1](=[O:38])([O:9][CH2:10]/[C:11](/[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:30][CH:29]=1)=[C:12](/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)\[CH2:13][OH:14])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8]

Participants

4

Reactant 1

HCID 588411855-bromopentyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate

Product 1

HCID 588411835-bromopentyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromopentyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate (1 eq) and PyrHF (excess) in MeCN (0.25 M) was stirred at rt for 2 h, diluted with 5 volumes of toluene, filtered through a pad of silica gel eluted with 70% EtOAc/hexanes to give the titled compound.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washeluted with 70% EtOAc/hexanes

Sources & evidence

ORD record
ord-81b749cc63e748858dfedd2a13c9dbe3
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

Loading…