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

HRID 1395
Notes
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Reaction equation

HRID 1395 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8857
Ethyl Acetate
Solvent

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-54921a0488e14a3e81bfab9c9a8565e8
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723666

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes