Trifluoroacetic acid → Ethyl 4-[1-(5,6,7,8-tetrahydro-3,5,5-trimethyl-8-oxo-2-naphthalenyl)-ethenyl]benzoate

HRID 51164Notes

Reaction equation

HRID 51164 reaction equation
[CH3:1][C:2]1[C:3]([C:15]([C:21]2[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=2)=[CH:16][Si](C)(C)C)=[CH:4][C:5]2[C:6](=[O:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.FC(F)(F)C(O)=O>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([C:15]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=2)=[CH2:16])=[CH:4][C:5]2[C:6](=[O:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54456954HCID 54456954, compound

Product 1

HCID 12106143Ethyl 4-[1-(5,6,7,8-tetrahydro-3,5,5-trimethyl-8-oxo-2-naphthalenyl)-ethenyl]benzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-[1-(5,6,7,8-tetrahydro-3,5,5-trimethyl-8-oxo-2naphthalenyl)-2-trimethylsilyl-ethenyl]benzoate (12.0 g, 27.6 mmol) in dichloromethane (900 mL) was treated with trifluoroacetic acid (100 mL) at 0° C. The mixture was stirred for 18 hours and allowed to reach room temperature. The mixture was diluted with toluene (˜100 mL) and concentrated. The residue was purified by silica gel chromatography (8×15 cm, 0 to 5% ethyl acetate/toluene) to afford the title material as a yellowish solid which was triturated in hexane (9.7 g, 97%). An analytical sample was recrystallized in hexane.

Workup

  1. customto reach room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (8×15 cm, 0 to 5% ethyl acetate/toluene)

Sources & evidence

ORD record
ord-838d9bd4edde481e85f3a1e473bca191
Source dataset
uspto-grants-2004_03
Patent number
US06713515B2

Reaction notes

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