Diisobutylaluminum hydride → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

HRID 250222ノート

反応式

HRID 250222 の反応式
C[O:2][C:3]([C:5]1[C:6]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])=[N:7][O:8][C:9]=1[CH:10]1[CH2:12][CH2:11]1)=O.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[CH:10]1([C:9]2[O:8][N:7]=[C:6]([C:13]3[C:14]([Cl:20])=[CH:15][CH:16]=[CH:17][C:18]=3[Cl:19])[C:5]=2[CH2:3][OH:2])[CH2:12][CH2:11]1

参加物

5

反応物 2

HCID 14487Diisobutylaluminum hydride2 回HCID 53421832Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate

生成物 1

HCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol収率 93%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a 0° C. solution of 5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (0.80 g, 2.6 mmol) in THF (8 mL) is added a 1M DIBAL solution in toluene (5.66 mL). The reaction is stirred one hour. An additional 1M DIBAL solution in Toluene (5.66 mL) is added and the reaction is stirred for an additional hour. The reaction is quenched with methanol and is acidified with aqueous HCl solution (1M). The aqueous solution is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure to yield the title compound (0.68 g, 93%). ES/MS m/e 284.0 (M+1).

後処理

  1. stirringthe reaction is stirred for an additional hour
  2. customThe reaction is quenched with methanol
  3. extractionThe aqueous solution is extracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-0fe56a33907240fda7b6055c5eedf1a7
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

反応ノート

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