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

HRID 1516199노트

반응식

HRID 1516199 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 aluminium hydride (2.03 g, 53.4 mmol) in five portions. After 1 h the reaction mixture was quenched dropwise with Seignette salt solution. The reaction mixture was filtered and the filtrate extracted with ethyl acetate. The combined organic extracts were washed with Seignette 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]+.

후처리

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

출처 및 근거

ORD 기록
ord-969adb7d5439425896bb00e5be94a795
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227461B2

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