Tetrabutylammonium Fluoride → 2-Ethynylbicyclo(2.2.1)heptan-2-ol

HRID 1398532Notes

Reaction equation

HRID 1398532 reaction equation
C[Si]([C:5]#[C:6][C:7]1([OH:14])[CH2:12][CH:11]2[CH2:13][CH:8]1[CH2:9][CH2:10]2)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:6]([C:7]1([OH:14])[CH2:12][CH:11]2[CH2:13][CH:8]1[CH2:9][CH2:10]2)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 700746122-((Trimethylsilyl)ethynyl)bicyclo[2.2.1]heptan-2-ol

Product 1

HCID 143098132-Ethynylbicyclo(2.2.1)heptan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-((trimethylsilyl)ethynyl)bicyclo[2.2.1]heptan-2-ol (700 mg, 5.1 mmol) was dissolved in THF (25 mL) and treated with TBAF (2.7 g, 10.2 mmol) at 0° C. for 30 min. Purification by gel chromatography afforded the title compound; 1H NMR (400 MHz, DMSO) delta 1.15-1.44 (m, 4H), 1.64-1.67 (m, 1H), 1.88-1.93 (m, 2H), 2.07-2.22 (m, 3H), 3.25 (s, 1H)

Workup

  1. customPurification by gel chromatography

Sources & evidence

ORD record
ord-0279d084c2aa49e9809c98ecef08f078
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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