Water → 1-(2-Phenyl-benzoxazol-6-yl)butan-1-one

HRID 1619944Notes

Reaction equation

Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([Li])CCC.CON(C)[C:25](=[O:29])[CH2:26][CH2:27][CH3:28].O>C1COCC1.CCCCCC>[C:9]1([C:7]2[O:8][C:4]3[CH:3]=[C:2]([C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH:16]=[CH:15][C:5]=3[N:6]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -70 °C

Procedure

10.00 g (36.48 mmol) 6-bromo-2-phenyl-benzoxazole are dissolved in 180 ml THF and cooled to −70° C., and 35.00 ml (56.00 mmol) n-butyl lithium 1.6M in hexane are added dropwise. This solution cooled to −70° C. is added dropwise after 20 min to an equally cold −70° C. solution of 2.5 g (19.1 mmol) N-methoxy-N-methyl-butyramide and 20 ml THF. After 20 min further stirring the mixture is mixed with water and allowed to come up to RT. The reaction mixture is extracted with water and DCM, the org. phase is dried on magnesium sulphate and the solv. is eliminated by rotary evaporation i.V. The residue is separated through silica gel (eluant cyclohexane/EA).

Workup

temperatureThis solution cooled to −70° C.
customto come up to RT
extractionThe reaction mixture is extracted with water and DCM
customphase is dried on magnesium sulphate
customThe residue is separated through silica gel (eluant cyclohexane/EA)

Sources & evidence

ORD record: ord-992bd95e5141421d8d06238ce1f88e49
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772323B2

Reaction notes

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