Trifluoroacetic acid → HCID 72714573, compound

HRID 1775767Notes

Reaction equation

HRID 1775767 reaction equation
[CH3:1][CH:2]([CH2:14]/[C:15](=[CH:23]/[C:24](/[CH3:39])=[CH:25]/[CH:26]([CH3:38])[CH2:27][CH:28]([CH3:37])[CH2:29][CH:30]([CH3:36])[CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])/[C:16]([O:18]C(C)(C)C)=[O:17])[C:3]([O:5][CH2:6][C:7]([O:9]C(C)(C)C)=[O:8])=[O:4].FC(F)(F)C(O)=O>ClCCl>[C:7]([CH2:6][O:5][C:3](=[O:4])[CH:2]([CH3:1])[CH2:14]/[C:15](=[CH:23]/[C:24](/[CH3:39])=[CH:25]/[CH:26]([CH3:38])[CH2:27][CH:28]([CH3:37])[CH2:29][CH:30]([CH3:36])[CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])/[C:16]([OH:18])=[O:17])([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734746HCID 131734746, compound

Product 1

HCID 72714573HCID 72714573, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Step 2) To 1-(2-tert-butoxy-2-oxoethyl) 5-tert-butyl (Z)-2-methyl-4-{(E)-2,4,6,8,10-pentamethyldodec-2-enylidene}pentanedioate (14.7 mg, 0.027 mmol) obtained in Step 1, dichloromethane (2 mL) and trifluoroacetic acid (0.2 mL, 2.6 mmol) were added, and the resulting mixture was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by thin-layer column chromatography (methanol/chloroform=1/9), whereby Compound 9 (8.6 mg, 74%) was obtained.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was purified by thin-layer column chromatography (methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-73e6015b90f14ee8b546fc1f0fcee27c
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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