Tetrabutylammonium Fluoride → 4-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoic acid

HRID 233110

Reaction equation

HRID 233110 reaction equation
[OH:1][C:2]1(C(OCC)=O)[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[C:7](C)=[C:6]([C:15]#[C:16][C:17]3[CH:31]=[CH:30][C:20]([C:21]([O:23]CC[Si](C)(C)C)=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[F-].C([N+](CC[CH2:53][CH3:54])(CCCC)CCCC)CCC>C1COCC1>[OH:1][C:2]1([CH2:20][C:21]([O:23][CH2:53][CH3:54])=[O:22])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:15]#[C:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70151178Trimethylsilylethyl 4-((5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 183145664-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.25 g (0.49 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate (Compound 117) in 5 ml of dry THF (flushed with argon) was added 1.48 ml (1.5 mmol) of tetrabutyl ammonium fluoride (1M solution in THF). The reaction mixture was stirred at room temperature for 12 hours, concentrated in vacuo to an oil and slowly diluted with water. The solution was acidified to pH 4 with 10% HCl and extracted with Et2O. The organic layer was dried over Na2SO4, concentrated in vacuo to an oil and purified by flash chromatography (silica, 90% EtOAc-hexane) to give the title compound as a white solid.

Workup

  1. concentrationconcentrated in vacuo to an oil
  2. additionslowly diluted with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo to an oil
  6. custompurified by flash chromatography (silica, 90% EtOAc-hexane)

Sources & evidence

ORD record
ord-9622d3d76ba94a848f7d85d394c752e5
Source dataset
uspto-grants-1997_01
Patent number
US05591858

Linked notes

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