Trifluoroacetic acid → HCID 67341904, compound

HRID 1669320Notes

Reaction equation

HRID 1669320 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Br:26])[CH:19]=2)(O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Br:26])[CH:19]=2)=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67341991HCID 67341991, compound

Product 1

HCID 67341904HCID 67341904, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[1-(3-bromo-4-methoxy-phenyl)-1-hydroxy-heptyl]-benzoic acid methyl ester (572 mg, 1.31 mmol) in dichloromethane (10 mL) is added TFA (749 mg, 6.57 mmol). 5 min later, triethylsilane (763 mg, 6.57 mmol) is added dropwise. 5 h later, the reaction mixture is diluted with ethyl acetate, washed with 1N NaOH, water, brine, dried over sodium sulfate, concentrated and purified by column chromatography to give 4-[1-(3-bromo-4-methoxy-phenyl)-hept-1-enyl]-benzoic acid methyl ester (380 mg), which is hydrolyzed by 5N NaOH (1 mL) to afford the titled compound (380 mg).

Workup

  1. washwashed with 1N NaOH, water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-34cd0b7b8ccd48a18e2ace01e6619028
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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