1,3-Dibromopropane → Ethyl 4-(3-bromopropoxy)mandelate

HRID 613406

反応式

HRID 613406 の反応式
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:15][CH2:16][CH2:17][CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

生成物 1

HCID 22459007Ethyl 4-(3-bromopropoxy)mandelate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of ethyl 4-hydroxymandelate (19.6 g, 0.1 mol), 1,3-dibromopropane (60.75 g, 0.3 mol) and cesium carbonate (35.75 g, 0.11 mol) in dry DMF (200 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and 1.0 N HCl. The organic layer was washed twice with water, once with brine and then dried over sodium sulfate. The organic layer was then filtered and the solvent remove in vacuo. The resulting oil was chromatographed on silica gel, using a gradient of 100% hexane to methylene chloride/hexane (2:1) to yield the titled compound.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and 1.0 N HCl
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was then filtered
  5. customthe solvent remove in vacuo
  6. customThe resulting oil was chromatographed on silica gel

出典と根拠

ORDレコード
ord-5c10bb06eaa1482ebdd2b2ca1e56472a
出典データセット
uspto-grants-1999_12
特許番号
US06008237

関連ノート

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