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

HRID 1619944노트

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HRID 1619944 반응식
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

참가 물질

7

반응물 4

HCID 962WaterHCID 13704543N-Methoxy-N-methylbutyramideHCID 230259476-Bromo-2-phenylbenzo[d]oxazoleHCID 178418339Butyllithium

생성물 1

HCID 674660111-(2-Phenyl-benzoxazol-6-yl)butan-1-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
-70 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-992bd95e5141421d8d06238ce1f88e49
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772323B2

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