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

HRID 1619944ノート

反応式

HRID 1619944 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-992bd95e5141421d8d06238ce1f88e49
出典データセット
uspto-grants-2014_07
特許番号
US08772323B2

反応ノート

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