Tetrabutylammonium Fluoride → 2-[3-(4,5-dihydro-4(R)-phenyl-oxazol-2-yl)phenoxy]ethan-1-ol

HRID 2395379Notes

Reaction equation

HRID 2395379 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[O:19][CH2:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:22]=2)[CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:23]1([C@@H:21]2[CH2:20][O:19][C:18]([C:14]3[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=3)[O:11][CH2:10][CH2:9][OH:8])=[N:22]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 186655451-(tert-butyldimethylsilyloxy)-2-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)phenoxy]ethane

Product 1

HCID 186655472-[3-(4,5-dihydro-4(R)-phenyl-oxazol-2-yl)phenoxy]ethan-1-olYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butyldimethylsilyloxy)-2-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)phenoxy]ethane (4.4 g, 11 mmol) in THF (35 ml) was added dropwise tetrabutylammonium fluoride (1M in THF, 14 ml). The reaction mixture was stirred at room temperature for 45 min., solvent removed by evaporation and the resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:2) to afford 2-[3-(4,5-dihydro-4(R)-phenyl-oxazol-2-yl)phenoxy]ethan-1-ol (2.8 g, 91%) as a colorless oil.

Workup

  1. customsolvent removed by evaporation
  2. customthe resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:2)

Sources & evidence

ORD record
ord-037db38096c642d5b71a84f36874a696
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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