HCID 58841169, compound → HCID 57446831, compound

HRID 1269349Notes

Reaction equation

HRID 1269349 reaction equation
[C:1](=[O:37])([O:8][CH2:9]/[C:10](/[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1)=[C:11](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)\[CH2:12][O:13][Si](C(C)(C)C)(C)C)[O:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7]>CC#N.C1(C)C=CC=CC=1>[C:1](=[O:37])([O:8][CH2:9]/[C:10](/[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:29][CH:28]=1)=[C:11](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)\[CH2:12][OH:13])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7]

Participants

4

Reactant 1

HCID 58841169HCID 58841169, compound

Product 1

HCID 57446831HCID 57446831, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.7 g of 4-bromobutyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate and 5 mL of PyHF in 100 mL of MeCN was stirred at rt for 2 h, diluted with 500 mL of toluene, filtered through a pad of silica gel, evaporated, and purified by flash chromatography to afford 4.3 g of the titled compound. 1H NMR (acetone-d6, 500 MHz): δ 7.70 (d, 2 H), 7.36 (d, 2 H), 7.18–7.10 (m, 5 H), 5.30 (s, 2 H), 4.68 (d, 2 H), 4.15 (t, 1 H, OH), 4.13 (t, 2 H), 3.53 (t, 2 H), 3.07 (s, 3 H), 1.93–1.87 (m, 2 H), 1.80–1.70 (m, 2 H).

Workup

  1. filtrationfiltered through a pad of silica gel
  2. customevaporated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e018c332dc9f417984d20e122944f532
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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