4-Pentenal → 1,8-Nonadien-5-ol

HRID 16225

反応式

HRID 16225 の反応式
[CH2:1]([Mg]Br)[CH2:2][CH:3]=[CH2:4].[CH:7](=[O:12])[CH2:8][CH2:9][CH:10]=[CH2:11]>O1CCCC1>[CH2:4]=[CH:3][CH2:2][CH2:1][CH:7]([OH:12])[CH2:8][CH2:9][CH:10]=[CH2:11]

参加物

4

反応物 2

HCID 164184-PentenalHCID 178418797HCID 178418797、化合物

生成物 1

HCID 118295421,8-Nonadien-5-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-Butenyl-magnesium bromide (125 mL, 0.5 M in tetrahydrofuran, 62.5 mmol) was added drop wise to a stirred and cooled (−78° C.) solution of pent-4-enal (4 g, 48.07 mmol) in dry tetrahydrofuran (160 mL). After the addition, the solution was warmed to room temperature and then quenched with NH4Cl solution. The mixture was partitioned with diethyl ether and the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 5-15% diethyl ether in hexanes to give the title compound as an oil.

後処理

  1. additionAfter the addition
  2. customquenched with NH4Cl solution
  3. customThe mixture was partitioned with diethyl ether
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified over silica gel using 5-15% diethyl ether in hexanes

出典と根拠

ORDレコード
ord-e98f6149fafa44c789cdbd4327d485dc
出典データセット
uspto-grants-2010_06
特許番号
US07737137B2

関連ノート

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