Aluminium lithium hydride → (3-Butyl-5-methyl-isoxazol-4-yl)-methanol

HRID 1695361ノート

反応式

HRID 1695361 の反応式
C([O:3][C:4]([C:6]1[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:8][O:9][C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:12]([C:7]1[C:6]([CH2:4][OH:3])=[C:10]([CH3:11])[O:9][N:8]=1)[CH2:13][CH2:14][CH3:15]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 665992233-Butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

生成物 1

HCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanol収率 95.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 3-butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester (9.8 g, 46.3 mmol) in THF (100 mL) under argon and at 0° C. was added lithium aluminum hydride (2.03 g, 53.4 mmol) in five portions. After 1 h the reaction mixture was quenched dropwise with Seignette's salt solution. The reaction mixture was filtered and the filtrate extracted with ethyl acetate. The combined organic extracts were washed with Seignette's salt solution then dried, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 4:6) afforded the title compound (7.5 g, 95%) as a yellow liquid. MS: m/e=170.3 [M+H]+.

後処理

  1. customAfter 1 h the reaction mixture was quenched dropwise with Seignette's salt solution
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate extracted with ethyl acetate
  4. washThe combined organic extracts were washed with Seignette's salt solution
  5. customthen dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 4:6)

出典と根拠

ORDレコード
ord-2b66920a74d94d0b9fa1f31f9d290ade
出典データセット
uspto-grants-2012_04
特許番号
US08163728B2

反応ノート

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