HCID 68836040, compound → HCID 68831604, compound

HRID 1454092Notes

Reaction equation

HRID 1454092 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:12]([O:11][C:9](=[O:10])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH2:19][C:20]([OH:22])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 68836040HCID 68836040, compound

Product 1

HCID 68831604HCID 68831604, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 1-benzyl 4-tert-butyl 2-(4-bromophenyl)succinate (2.00 g, 4.77 mmol) and silica gel (23.8 g) in toluene (100 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 (1.53 g, 88%). LC/MS: 3.43 min; z/e 361 and 363, calcd (M−1) 361 and 363. 1H NMR (400 MHz: DMSO-d6): 7.55 (2H), 7.30 (7H), 5.10 (2H), 4.05 (1H), 3.05 (1H), 2.65 (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-f3b805d0dfbe4b6fbb8d302e4eaaa62a
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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