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

HRID 1375705Notes

Reaction equation

HRID 1375705 reaction equation
[C:1]([O:4][CH2:5]/[C:6](/[C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[C:7](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[CH2:8][O:9][Si](C(C)(C)C)(C)C)(=[O:3])[CH3:2]>CC#N.C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5]/[C:6](/[C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1)=[C:7](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[CH2:8][OH:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 58787781(2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate

Product 1

HCID 58787789(2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetateYield 99.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 50.5 g of (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate in 125 mL of MeCN, 10 mL of PyHF was added and the resulted mixture was stirred at rt for 1.5 hr. The reaction mixture was diluted with 600 mL of toluene and then loaded on silica gel column and eluted with EtOAc. The solvent was evaporated to afford 38.3 g of the titled compound. 1H NMR (acetone-d6, 500 M Hz): δ 7.68 (d, 2H), 7.32 (d, 2H), 7.15–7.00 (m, 5H), 5.20 (s, 2H), 4.62 (d, 2H), 4.09 (t, 1H, OH), 3.02 (s, 3H), 1.92 (s, 3 H),

Workup

  1. washeluted with EtOAc
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-af05a29582e3402987d67f32642aaed4
Source dataset
uspto-grants-2007_01
Patent number
US07169809B2

Reaction notes

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