Methyl iodide → Methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine

HRID 38382

反応式

HRID 38382 の反応式
[C:1]([O-:4])([O-])=O.[K+].[K+].[O:7]1[C:12]2[CH:13]=[CH:14][C:15](O)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1.I[CH3:19]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C>[CH3:19][CH:9]1[O:10][C:11]2[CH:16]=[CH:15][C:14]([O:4][CH3:1])=[CH:13][C:12]=2[O:7][CH2:8]1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

生成物 1

HCID 21624819Methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine収率 85%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of K2CO3 (47.54 g, 344 mmol) and Bu4NI (1.256 g, 3.4 mmol) in DMF was added 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.2 g, 172 mmol) followed by iodomethane (16.1 ml, 258 mmol). After 16 hours the mixture was filtered. The solution was mixed with H2O and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography (95:5 hexane/ethyl acetate) afforded methyl 6-methoxy-2,3-dihydro-benzo[1,4]dioxine (24.23 g, 85%) as a clear oil.

後処理

  1. filtrationAfter 16 hours the mixture was filtered
  2. additionThe solution was mixed with H2O
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography (95:5 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-88354675dfb54aa5b93c85ab368323b4
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

読み込み中…