Aluminium lithium hydride → benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

HRID 1179485ノート

反応式

HRID 1179485 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26](OC)=[O:27])=[CH:20][CH:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[OH:27][CH2:26]/[CH:25]=[CH:24]/[C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:19][CH:20]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 58978081methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate

生成物 1

HCID 58978090benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

A THF solution of LiAlH4 (6.75 mL of a 1.0 M solution, 6.75 mmol) was added to a cooled (−78° C.) solution of methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate (2.1 g, 6.75 mmol) in TBF (34 mL). The solution was allowed to warm slowly to −20° C. and maintained at that temperature for 2 hours. The reaction mixture was quenched by slow addition of saturated NH4Cl and then treated with dilute citric acid. The resulting solution was stirred for 15 minutes and then extracted with three portions of ethyl acetate. The combined organic phases were washed with H2O, brine and dried (MgSO4), filtered and concentrated to give an oil. The crude product was purified by column chromatography (20-50% ethyl acetate-hexane) to provide the title compound as a yellow solid.

後処理

  1. temperaturemaintained at that temperature for 2 hours
  2. customThe reaction mixture was quenched by slow addition of saturated NH4Cl
  3. additiontreated with dilute citric acid
  4. extractionextracted with three portions of ethyl acetate
  5. washThe combined organic phases were washed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil
  10. customThe crude product was purified by column chromatography (20-50% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-b2e918b68efb4f408b03cca71023086a
出典データセット
uspto-grants-2007_10
特許番号
US07279494B2

反応ノート

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