Diethyl Ether → Methyl alpha-(2,6-diallyl-4-hydroxyphenoxy)4-chlorobenzeneacetate

HRID 9256

반응식

HRID 9256 반응식
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10]CC2C=CC=CC=2)[CH:7]=[C:6]([CH2:18][CH:19]=[CH2:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].Br[CH:23]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>CN(C=O)C>[CH2:18]([C:6]1[CH:7]=[C:8]([OH:10])[CH:9]=[C:4]([CH2:1][CH:2]=[CH2:3])[C:5]=1[O:21][CH:23]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])[CH:19]=[CH2:20]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetateHCID 219859512,6-Diallyl4-benzyloxyphenol

생성물 1

HCID 21985939Methyl alpha-(2,6-diallyl-4-hydroxyphenoxy)4-chlorobenzeneacetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2,6-diallyl-4-benzyloxyphenol (200 mg, 1.0 eq) in DMF (8 mL) were added methyl α-bromo-4-chlorobenzeneacetate (190 mg, 1.0 eq) and Cs2CO3 (285 mg, 1.2 eq). The reaction mixture was stirred at room temperature for 15 h, poured into ether, washed with water and brine, dried over MgSO4, filtered, and concentrated in vac. Purification by chromatography (SiO2, EtOAc/Hexanes 1:20) afforded the desired methyl α-(2,6-diallyl-4-hydroxyphenoxy)-4-chlorobenzeneacetate.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vac
  5. customPurification by chromatography (SiO2, EtOAc/Hexanes 1:20)

출처 및 근거

ORD 기록
ord-cbe90fa9d62e4ab79ebe977953f20624
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091230B2

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