Tetrabutylammonium Fluoride → HCID 18665560, compound

HRID 2395389Notes

Reaction equation

HRID 2395389 reaction equation
[Si]([O:8][C:9]1[C:10]([F:26])=[C:11]([C:15]2[O:16][C@H:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][N:19]=2)[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:26][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[CH:12][C:11]=1[C:15]1[O:16][C@H:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][N:19]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18665557HCID 18665557, compound

Product 1

HCID 18665560HCID 18665560, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-tert-butyldimethylsilyloxy-2-fluorophenyl)-4,5-dihydro-5(R)-phenyloxazole (2.2 g, 5.8 mmol) in THF (20 ml) was added dropwise tetrabutylammonium fluoride (1M in THF, 7 ml). The reaction mixture was stirred at ambient temperature for 10 min., volatiles removed by evaporation and the resulting residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (3:2) to afford the title compound (1.3 g, 86%) as colorless solids.

Workup

  1. customvolatiles removed by evaporation
  2. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (3:2)

Sources & evidence

ORD record
ord-c9955f4c0e51410e9fc212a0142ee329
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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