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

HRID 613406

반응식

HRID 613406 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 22459007Ethyl 4-(3-bromopropoxy)mandelate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c10bb06eaa1482ebdd2b2ca1e56472a
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008237

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