Methylenechloride Hexane → 2-Isopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-8,8-dimethylquinoline

HRID 324883ノート

反応式

HRID 324883 の反応式
[CH:1]([C:4]1[C:13]([C:14](OCC)=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:27])([CH3:26])[C:6]=2[N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(Cl)Cl.CCCCCC>C1COCC1>[CH:1]([C:4]1[C:13]([CH2:14][OH:15])=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:27])([CH3:26])[C:6]=2[N:5]=1)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 21226440Methylenechloride HexaneHCID 21226445Aluminium lithium hydrideHCID 220050562-Isopropyl-3-carboethoxy-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-8,8-dimethylquinoline

生成物 1

HCID 220050492-Isopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-8,8-dimethylquinoline収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the intermediate obtained in Step B (1.32 g, 3.6 mmol) in THF (35 mL) was added lithium aluminum hydride (1 M/THF, 2 eq., 7.2 mL) dropwise. The reaction was refluxed for 1.5 hours and cooled to room temperature. Then the reaction was quenched with water and the THF was evaporated. The residue was partitioned between diethyl ether (150 mL) and water (100 mL). The organic layer was washed with brine (1×100 mL), dried with MgSO4, filtered, and concentrated to afford a solid. Flash chromatography (40% CH2Cl2/hexane) afforded the title compound as a white solid (808 mg, 2.5 mmol, 70%). 1H NMR (300 MHz, CDCl3): δ 7.13 (d, J=7.0 Hz, 4H), 4.36 (d, J=5.5 Hz, 2H), 3.42 (septet, J=6.6 Hz, 1H), 2.24 (t, J=5.5 Hz, 2H), 1.67 (m, 4H), 1.32 (m, 13H). FAB-MS: calculated for (C21H26FNO) 327, found 328 (M+H). mp 146-149° C. Rf=0.2 (50% CH2Cl2/hexane).

後処理

  1. temperatureThe reaction was refluxed for 1.5 hours
  2. customThen the reaction was quenched with water
  3. customthe THF was evaporated
  4. customThe residue was partitioned between diethyl ether (150 mL) and water (100 mL)
  5. washThe organic layer was washed with brine (1×100 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a solid

出典と根拠

ORDレコード
ord-323622702e754381a1102e9f24019b74
出典データセット
uspto-grants-2001_04
特許番号
US06218431B1

反応ノート

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