HCID 58841164, compound → HCID 58841178, compound

HRID 1269352Notes

Reaction equation

HRID 1269352 reaction equation
[C:1](=[O:39])([O:10][CH2:11]/[C:12](/[C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)=[C:13](/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)\[CH2:14][O:15][Si](C(C)(C)C)(C)C)[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9]>C(#N)C.C1(C)C=CC=CC=1>[C:1](=[O:39])([O:10][CH2:11]/[C:12](/[C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:31][CH:30]=1)=[C:13](/[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)\[CH2:14][OH:15])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9]

Participants

4

Reactant 1

HCID 58841164HCID 58841164, compound

Product 1

HCID 58841178HCID 58841178, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 24 g of 6-bromohexyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate in 200 mL of acetonitrile was added 9 mL of PyrHF and the mixture was stirred at 25° C. for 1.5 h. The reaction mixture was diluted with 1 L of toluene, loaded on silica gel and washed with EtOAc. The solvent was evaporated to afford 16.8 g of the titled compound. The crude compound was used directly for the next step.

Workup

  1. washwashed with EtOAc
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-383b8933086d4295ac6ae01835d8a324
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

Loading…