Tetrabutylammonium Fluoride → 2-(4-Tetrahydropyranyloxy-2-butynyl)cyclopropylmethanol

HRID 36806Notes

Reaction equation

HRID 36806 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[CH2:13][C:14]#[C:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[O:17][CH2:16][C:15]#[C:14][CH2:13][CH:11]1[CH2:12][CH:10]1[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 544958342-(4-Tetrahydropyranyloxy-2-butynyl)cyclopropylmethyl t-butyldimethylsilyl ether

Product 1

HCID 541873012-(4-Tetrahydropyranyloxy-2-butynyl)cyclopropylmethanolYield 111.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 2-(4-tetrahydropyranyloxy-2-butynyl)cyclopropylmethyl t-butyldimethylsilyl ether (5.8 g, 17.2 mmol) was dissolved in tetrahydrofuran (50 ml), and a tetrabutyl ammonium fluoride (factor=1.0) tetrahydrofuran solution (33 ml, 33 mmol) was added thereto at 0° C. The mixture was stirred for one hour. The product was purified by column chromatography to obtain 2-(4-tetrahydropyranyloxy-2-butynyl)cyclopropylmethanol (4.3 g).

Workup

  1. customat 0° C
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-d3861bc5992545ccab869e2c4699f880
Source dataset
uspto-grants-1995_05
Patent number
US05416231

Reaction notes

Loading…