2',4'-Dihydroxyacetophenone → 4'-Benzyloxy-2'-hydroxyacetophenone

HRID 858662ノート

反応式

HRID 858662 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[C:23](=[O:25])[CH3:24]>CN(C=O)C>[CH2:7]([O:22][C:20]1[CH:19]=[CH:18][C:17]([C:23](=[O:25])[CH3:24])=[C:16]([OH:15])[CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

生成物 1

HCID 3092574'-Benzyloxy-2'-hydroxyacetophenone収率 60.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (27.2 g, 0.2 mol) followed by benzyl bromide (7.04 mL, 59.2 mmol) were added to a solution of 1-(2,4-dihydroxy-phenyl)-ethanone (10 g, 66 mmol) in DMF (90 mL): The mixture was stirred for 2 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) followed by recrystallization gave the title compound as a white solid (8.7 g, 55%). 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3 H), 5.09 (s, 2 H), 6.50 (s, 1 H), 6.51 (dd, J=9.1, 3.9 Hz, 1 H), 7.34–7.43 (m, 5 H), 7.64 (d, J=9.1 Hz, 1 H), 12.73 (s, 1 H).

後処理

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)
  6. customfollowed by recrystallization

出典と根拠

ORDレコード
ord-fe87ee52d494475cb97c0477906d1d46
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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