Tetrabutylammonium Fluoride → 4-([(5,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoic acid

HRID 2415601Notes

Reaction equation

HRID 2415601 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([O:19][C:20]3[CH:34]=[CH:33][C:23]([C:24]([O:26]CC[Si](C)(C)C)=[O:25])=[CH:22][CH:21]=3)=[O:18])[CH:5]=[CH:4][C:3]1=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[CH3:1][C:2]1([CH3:35])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([O:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:33][CH:34]=3)=[O:18])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 106016292-Trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate

Product 1

HCID 99530614-([(5,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate (Compound E10, 100.0 mg, 0.198 mmol) in 2.0 mL THF at room temperature was added 1553 mg of tetrabutylammonium fluoride (0.594 mmol 0.6 mL of a 1M solution in THF). After stirring overnight the reaction was diluted with EtOAc and washed with H2O and saturated aqueous NaCl before being dried over MgSO4. The solvents were removed under reduced pressure and the residue washed with hot acetonitrile leaving the product as a colorless solid.

Workup

  1. washwashed with H2O and saturated aqueous NaCl
  2. dry with materialbefore being dried over MgSO4
  3. customThe solvents were removed under reduced pressure
  4. washthe residue washed with hot acetonitrile leaving the product as a colorless solid

Sources & evidence

ORD record
ord-f255f923320643e5943989f11d6619e7
Source dataset
uspto-grants-2004_11
Patent number
US06818775B2

Reaction notes

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