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

HRID 1056896노트

반응식

HRID 1056896 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 (1 10 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 a2S04, 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. customdried over a2S04
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-0cf80fff50014e45a675eaa746725989
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399651B2

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