Toluene → [5-Cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol

HRID 2423409ノート

反応式

HRID 2423409 の反応式
[CH:1]1([C:6]2[O:10][N:9]=[C:8]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[C:7]=2[C:19](OCC)=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH:1]1([C:6]2[O:10][N:9]=[C:8]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[C:7]=2[CH2:19][OH:20])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

7

反応物 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 21225700Diisobutylaluminumhydride2 回HCID 59321583Ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate

生成物 1

HCID 59709035[5-Cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol収率 96.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate (3.0 g, 8.6 mmol) in tetrahydrofuran (35 mL) at 0° C. was added a 1.5 M solution of diisobutylaluminum hydride in toluene (8.6 mL, 13 mmol) dropwise. The solution was allowed to stir while warming slowly for approximately 3.5 hours and was re-cooled to 0° C. An additional portion of diisobutylaluminum hydride (4.3 mL, 6.5 mmol) was added and the solution was allowed to stir for an additional 35 minutes. Then Rochelle's salt (40 mL) was added slowly at 0° C. followed by some ethyl acetate. The mixture was allowed to warm to ambient temperature and stirred overnight. The layers were separated and the ethyl acetate was washed with brine, dried over magnesium sulfate and concentrated to afford [5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol (2.59 g, 82%). 1H-NMR (400 MHz, DMSO-d6) δ 7.61-7.51 (m, 3H), 4.85 (t, J=5 Hz, 1H), 4.14 (d, J=5 Hz, 2H), 3.46-3.48 (m, 1H), 2.07-1.99 (m, 2H), 1.81-1.60 (m, 6H).

後処理

  1. temperaturewhile warming slowly for approximately 3.5 hours
  2. stirringto stir for an additional 35 minutes
  3. temperatureto warm to ambient temperature
  4. stirringstirred overnight
  5. customThe layers were separated
  6. washthe ethyl acetate was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0bd02ca00c9045e6835cac83358c76aa
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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