HCID 68834130, compound → HCID 68833438, compound

HRID 1454087Notes

Reaction equation

HRID 1454087 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:9]([OH:11])=[O:10])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 68834130HCID 68834130, compound

Product 1

HCID 68833438HCID 68833438, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-benzyl 1-tert-butyl 2-(4-bromophenyl)succinate (3.00 g, 7.15 mmol) and silica gel (35.7 g) in toluene (230 mL) was heated at reflux for 3 h. The crude mixture was cooled to room temperature and filtered. The filter cake was washed with dichloromethane/methanol (8:2; 2×100 mL) then the organic filtrates were combined and evaporated to dryness to give the title compound as a white solid (2.25 g, 87%). LC/MS: 3.41 min; z/e 361 and 363, calcd (M−1) 361 and 363. 1H NMR (400 MHz: CDCl3): 7.40 (2H), 7.30 (5H), 7.15 (2H), 5.10 (2H), 4.05 (1H), 3.15 (1H), 2.70 (1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered
  4. washThe filter cake was washed with dichloromethane/methanol (8:2; 2×100 mL)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-931e79e4b9c242cd8b19584981618ce0
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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