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

HRID 964467

反応式

HRID 964467 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 19080423Methyl alpha-(4-hydroxymethyl-2-n-propyl-phenoxy)-3,4-methylenedioxyphenylacetate収率 81,308,200%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3.84 g (23.13 nmole) 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.

後処理

  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

出典と根拠

ORDレコード
ord-66f5fa683fb44a3fb8fd1f8f42f399c2
出典データセット
uspto-grants-1998_06
特許番号
US05767310

関連ノート

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