Tetrabutylammonium Fluoride → 4-(3-Methylisoxazol-5-yl)butan-1-ol

HRID 1458352Notes

Reaction equation

HRID 1458352 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:18][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[O:17][N:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 221009045-[4-(Tert-butyldirnethylsilanyloxy)butyl]-3-methylisoxazole

Product 1

HCID 221009164-(3-Methylisoxazol-5-yl)butan-1-olYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[4-(tert-butyldirnethylsilanyloxy)butyl]-3-methylisoxazole (350 mg in 5 mL dry tetrahydrofuran) at 0° C. was added 1.62 mL of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and the mixture stirred while warming to room temperature. After 16 hours, the mixture was concentrated in vacuo and the residue purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:3, then 1:1) to give the title compound (147 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-a5ce27bcc5534cc5b3eedb0f54a1e2cf
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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