Acetophenone → 2-Phenyl-4-penten-2-ol

HRID 450962

반응식

HRID 450962 반응식
[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

참가 물질

4

반응물 2

HCID 7410AcetophenoneHCID 178455850HCID 178455850, 화합물

생성물 1

HCID 1437612-Phenyl-4-penten-2-ol수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19e7be6426b942bda5c4d5b18941ffbb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487094B2

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