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

HRID 571064ノート

反応式

HRID 571064 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2001c8329744bdd8ae044388884ee7d
出典データセット
uspto-grants-2015_05
特許番号
US09024032B2

反応ノート

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