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

HRID 24590

Reaction equation

HRID 24590 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 155.3 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-07d00019fadd48a794b13a9f88406220
Source dataset
uspto-grants-2005_02
Patent number
US06855832B2

Linked notes

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