Oxiranemethanol, 3-[(phenylmethoxy)methyl]- → 3-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

HRID 400233

反応式

HRID 400233 の反応式
[CH2:1]([O:8][CH2:9][CH:10]1[O:14][CH:11]1[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([Mg]Cl)[CH:16]=[CH2:17]>O1CCCC1>[CH2:17]([C:10]([OH:14])([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][CH2:12][OH:13])[CH:16]=[CH2:15]

参加物

4

反応物 2

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-HCID 178418473HCID 178418473、化合物

生成物 1

HCID 189441063-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

A solution of 4-benzyloxy-2,3-epoxy-1-butanol (6.28 g, 32.37 mmol) in anhydrous tetrahydrofuran (75 mL) was added dropwise at -40° C. over a period of 45 minutes, to a 2M solution of allyl magnesium chloride (48.5 mL, 97 mmol) and tetrahydrofuran (50 mL). The solution was stirred at -40° C. for 1 hour, warmed to 0° C. and quenched by addition of aqueous ammonium chloride solution. The tetrahydrofuran layer was separated and the aqueous layer was extracted with ethyl acetate (three times). The combined organic extract was dried (magnesium sulfate), filtered and concentrated to obtain a mixture of compounds A and B.

後処理

  1. temperaturewarmed to 0° C.
  2. customquenched by addition of aqueous ammonium chloride solution
  3. customThe tetrahydrofuran layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (three times)
  5. extractionThe combined organic extract
  6. dry with materialwas dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain

出典と根拠

ORDレコード
ord-757e5a1c8b554ab7918a14250606dd48
出典データセット
uspto-grants-1998_10
特許番号
US05827868

関連ノート

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