Tetrahydrofuran → HCID 70982963、化合物

HRID 338955ノート

反応式

HRID 338955 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.COC[C@@H](O)C>O>[CH3:17][O:13][CH2:14][C@H:15]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)[CH3:16]

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 132242-Methyl-8-hydroxyquinolineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6993459(2S)-1-methoxypropan-2-ol

生成物 1

HCID 70982963HCID 70982963、化合物収率 31.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 2-methylquinolin-8-ol (1.0 g, 6.3 mmol) in tetrahydrofuran (5.2 mL, 6.3 mmol) was added triphenylphosphine (6.9 g, 26 mmol), diethyl azodicarboxylate (1.6 mL, 10 mmol), and (S)-1-methoxypropan-2-ol (0.80 mL, 8.2 mmol) and the resultant mixture allowed to stir at ambient temperature for 24 hours. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by reverse phase chromatography on C18 (0-80% acetonitrile/water) afforded the title compound (0.46 g, 28%).

後処理

  1. extractionextracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined organic extracts dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by reverse phase chromatography on C18 (0-80% acetonitrile/water)

出典と根拠

ORDレコード
ord-ac379a2808554510a8b7462e6f3de3de
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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