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

HRID 1506410ノート

反応式

HRID 1506410 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e65ca4a69b3436aa34c3a5ac0e6f48d
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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