Tetrahydrofuran → 2-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one

HRID 1506410노트

반응식

HRID 1506410 반응식
C(C1C=C[C:10]2[C:9](=[O:13])[CH2:8][CH2:7][CH2:6][C:5]=2N=1)=C.C[N+:15]1([O-])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C1C[O:25][CH2:24]C1>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[OH:18][CH:19]([C:20]1[CH:6]=[CH:7][C:8]2[C:9](=[O:13])[CH2:10][CH2:5][CH2:17][C:16]=2[N:15]=1)[CH2:24][OH:25]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 671675322-vinyl-7,8-dihydroquinolin-5(6H)-one

생성물 1

HCID 671713442-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one수율 47%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 2-vinyl-7,8-dihydroquinolin-5(6H)-one (Preparation 54C, 0.400 g, 2.31 mmol) and N-methylmorpholine-N-oxide (50% in water, 0.479 mL, 2.31 mmol) in THF (11 mL) at room temperature was added osmium tetroxide (4% in water, 0.725 mL, 0.092 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (50 mL). The organic layer was washed with brine (50 mL), the combined aqueous layers were extracted with ethyl acetate (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one (0.226 g, 1.09 mmol, 47% yield) as a yellow oil. The compound had an HPLC ret. time=0.330 min. (condition A); LC/MS M+1=207.9.

후처리

  1. washwashed with water (50 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. extractionthe combined aqueous layers were extracted with ethyl acetate (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2e65ca4a69b3436aa34c3a5ac0e6f48d
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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