HCID 68838048, compound → HCID 68834075, compound

HRID 1454098Notes

Reaction equation

HRID 1454098 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:14]([O:16]C(C)(C)C)=[O:15])=[CH:9][CH:8]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]>C1(C)C=CC=CC=1>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][CH:13]([C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:1][CH2:2][CH:3]([CH3:4])[CH3:5])=[CH:12][CH:11]=1)[C:14]([OH:16])=[O:15])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 1

HCID 68838048HCID 68838048, compound

Product 1

HCID 68834075HCID 68834075, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-benzyl 1-tert-butyl 2-[4-(isopentyloxy)phenyl]succinate (2.00 g, 4.69 mmol) and silica gel (23.4 g) in toluene (150 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 white solid (1.41 g, 82%). LC/MS: 3.74 min; z/e 388, calcd (M+1) 388. The enantiomers were separated using a Chiralpak AD column (20% EtOH: Heptane: 0.1% TFA), Flow 20 mL/min, λ=215 nM Ent-1=12.5 min, Ent-2=15.0 min.

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-0d47490e1f174aa9994a147af60d1b9f
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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