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

HRID 610343

Reaction equation

HRID 610343 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 tetrabutylammonium 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-4ddcad34cad44c76bc5801e958684f0e
Source dataset
uspto-grants-1999_12
Patent number
US05998471

Linked notes

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