HCID 68833946, compound → HCID 68833938, compound

HRID 1454103Notes

Reaction equation

HRID 1454103 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[CH:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])=[CH:10][CH:11]=1)[CH2:26][C:27]([OH:29])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 68833946HCID 68833946, compound

Product 1

HCID 68833938HCID 68833938, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 1-benzyl 4-tert-butyl 2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)succinate (1.00 g, 2.12 mmol) and silica gel (10.6 g) in toluene (50 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 while solid (0.83 g, 94%). LC/MS: 4.03 min; z/e 432, calcd (M+18) 432. 1H NMR (400 MHz: DMSO-d6): 7.05 (7H), 6.60 (2H), 4.95 (2H), 3.85 (1H), 2.85 (1H), 2.40 (1H), 0.80 (9H), 0.00 (6H).

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-c118fb380aaf4875bd5ea36b2d6cd5ba
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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