Tetrabutylammonium Fluoride → alpha-Ethynylbenzenemethanol

HRID 1588714Notes

Reaction equation

HRID 1588714 reaction equation
C[Si]([C:5]#[C:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:6]([CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 27604161-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

Product 1

HCID 20155alpha-EthynylbenzenemethanolYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Place a mixture of α-[(trimethylsilyl)ethynyl]-benzene-methanol (4.09 g, 20 mmol) and tetrahydrofuran (25 mL) under argon atmosphere and cool to 0° C. Add, by dropwise addition, tetra-n-butylammonium fluoride (25 mL of a 1M solution in tetrahydrofuran, 25 mmol). Allow to warm to room temperature and stir for 1 hour. Partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride and concentrate in vacuo. Purify by silica gel chromatography (15% ethyl acetate/hexane) then purify further by distillation to yield 2.15 g of the title compound; bp 100°-110° C. @0.1 mm Hg.

Workup

  1. temperatureAllow to warm to room temperature
  2. customPartition between ethyl ether and water
  3. customSeparate the organic phase
  4. washwash with saturated aqueous sodium chloride
  5. concentrationconcentrate in vacuo
  6. customPurify by silica gel chromatography (15% ethyl acetate/hexane)
  7. distillationthen purify further by distillation

Sources & evidence

ORD record
ord-3a223550e8214c68a932503169f4d82d
Source dataset
uspto-grants-1993_06
Patent number
US05223518

Reaction notes

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