Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate → 4-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcohol

HRID 37233

反応式

HRID 37233 の反応式
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][C:8]=1[CH2:17][CH:18]=[CH2:19])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C:7]1[CH:16]=[CH:15][C:10]([CH2:11][OH:12])=[CH:9][C:8]=1[CH2:17][CH:18]=[CH2:19])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 544131774-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcohol収率 93.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a magnetically stirred solution of 8.523 g (28.0 mmol) of the product from Step C in 35 mL of anhydrous THF was added 15.0 mL of a 1.0M solution of lithium aluminum hydride in THF, and the reaction mixture was stirred under a nitrogen atmosphere for 2 hours. At this point, the reaction was quenched by cautious addition of 10 mL water, the resulting precipitate was dissolved by addition of 1.0N is hydrochloric acid and the product was extracted into ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo to afford 7.258 g (93%) of the title compound.

後処理

  1. customAt this point, the reaction was quenched by cautious addition of 10 mL water
  2. dissolutionthe resulting precipitate was dissolved by addition of 1.0N
  3. extractionthe product was extracted into ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-e4a9f528123b42bc910262d591370551
出典データセット
uspto-grants-1995_05
特許番号
US05420133

関連ノート

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