Acetophenone → 2-Phenyl-4-penten-2-ol

HRID 450962

反応式

HRID 450962 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C1COCC1>[C:4]1([C:1]([OH:3])([CH2:12][CH:11]=[CH2:10])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 7410AcetophenoneHCID 178455850HCID 178455850、化合物

生成物 1

HCID 1437612-Phenyl-4-penten-2-ol収率 99.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of acetophenone (30 g, 0.25 mol) in dry THF (250 mL) at −78° C. was added dropwise 1M allylmagnesium bromide (1.25 L, 1.25 mol). After addition was complete, the mixture was allowed to stir at rt for 3 h. The reaction was quenched with satd aq NH4Cl solution (30 mL). The mixture was extracted with EtOAc (200 mL). The organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to give 2-phenylpent-4-en-2-ol (40.2 g), which was used for the next step without purification.

後処理

  1. additionAfter addition
  2. customThe reaction was quenched with satd aq NH4Cl solution (30 mL)
  3. extractionThe mixture was extracted with EtOAc (200 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-19e7be6426b942bda5c4d5b18941ffbb
出典データセット
uspto-grants-2013_07
特許番号
US08487094B2

関連ノート

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