Acetonitrile → Prinaberel

HRID 491733

Reaction equation

HRID 491733 reaction equation
F.[Si]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]3[C:24]([CH:25]=[CH2:26])=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:12][C:11]=1[F:27])(C(C)(C)C)(C)C.C1C[O:31]CC1.C(#N)C>O>[F:27][C:11]1[CH:12]=[C:13]([C:16]2[O:17][C:18]3[C:24]([CH:25]=[CH2:26])=[CH:23][C:22]([OH:31])=[CH:21][C:19]=3[N:20]=2)[CH:14]=[CH:15][C:10]=1[OH:9]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 14917Hydrofluoric AcidHCID 866136662-(4-{[Tert-butyl(dimethyl)silyl]oxy}-3-fluorophenyl)-7-vinyl-1,3-benzoxazole

Product 1

HCID 656954PrinaberelYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Hydrofluoric acid (48 wt. % in water, 1 mL) was added into a solution of 5-{[tert-butyl)dimethyl)silyl]oxy}-2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorophenyl)-7-vinyl-1,3-benzoxazole (1.5 g, 3.0 mmol), THF (6 mL) and acetonitrile (3 mL). The reaction mixture was stirred at 65° C. for 8 h, and then poured into water. The precipitated solid was filtered oft and dried. Crystallization of the product from acetone/ethyl ether gave a white solid (0.72 g, 81% yield, m.p. 249-251° C.); MS m/e 272 (M+H)+.

Workup

  1. filtrationThe precipitated solid was filtered oft
  2. customdried
  3. customCrystallization of the product from acetone/ethyl ether

Sources & evidence

ORD record
ord-1005539dccac438f97327e0bb934516c
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Linked notes

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