Cesium carbonate → Methyl alpha-(4-hydroxymethyl-2-n-propyl-phenoxy)-3,4-methylenedioxyphenylacetate

HRID 865526

반응식

HRID 865526 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:20]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:20]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[C:21]([O:23][CH3:24])=[O:22])=[C:3]([CH2:10][CH2:11][CH3:12])[CH:4]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 220112094-(Hydroxymethyl)-2-propylphenol

생성물 1

HCID 19080423Methyl alpha-(4-hydroxymethyl-2-n-propyl-phenoxy)-3,4-methylenedioxyphenylacetate수율 81.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3.84 g (23.13 mmol) of 4-hydroxy-3-n-propylbenzyl alcohol dissolved in 70 mL of anhydrous DMF was added 9.04 g (27.7 mmol) of cesium carbonate and the reaction mixture was magnetically stirred at room temperature for 15 minutes. Methyl α-bromo-3,4-methylenedioxyphenylacetate (7.58 g; 27.7 mmol) was added and the reaction mixture was then stirred for an additional 14 hours at room temperature under a nitrogen atmosphere. The reaction was then partitioned between 5% aqueous citric acid (700 mL) and EtOAc (100 mL) and extracted. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 40% EtOAc-hexane. The purified fractions were combined, evaporated, and dried in vacuo to afford 6.74 g (81%) of the title compound as a yellow oil.

후처리

  1. stirringthe reaction mixture was then stirred for an additional 14 hours at room temperature under a nitrogen atmosphere
  2. customThe reaction was then partitioned between 5% aqueous citric acid (700 mL) and EtOAc (100 mL)
  3. extractionextracted
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 40% EtOAc-hexane
  11. customevaporated
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-f66e4b0dbcdd4e3eac1278977119a308
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565485

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