5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one → 5-(Benzyloxy)-2-methyl-4H-pyran-4-one

HRID 571064노트

반응식

HRID 571064 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15]Cl)[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[NH4+].[Cl-].[Zn]>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH3:15])[O:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 37033215-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

생성물 1

HCID 53141715-(Benzyloxy)-2-methyl-4H-pyran-4-one수율 42%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 25517Ammonium Chloride용매

반응 조건

온도
70 °C

실험 절차

To a suspension of 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one (110 g, 0.44 mol) in saturated aqueous NH4Cl (1 L) was added Zn powder (58.5 g, 0.9 mol) at r.t. and the mixture was stirred at 70° C. for 2 h. The mixture was partitioned between water and EtOAc, the EtOAc phase was collected and water phase was extracted with EtOAc twice. The combined EtOAc layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography to give 40 g (42%) of 5-(benzyloxy)-2-methyl-4H-pyran-4-one.

후처리

  1. customThe mixture was partitioned between water and EtOAc
  2. customthe EtOAc phase was collected
  3. extractionwater phase was extracted with EtOAc twice
  4. washThe combined EtOAc layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-d2001c8329744bdd8ae044388884ee7d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024032B2

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