Water → 4-Allyloxy-2-ethoxy-1,3-benzodioxolane

HRID 218264ノート

反応式

HRID 218264 の反応式
[CH2:1]([O:3][CH:4]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:6]=2[O:5]1)[CH3:2].[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].O>CN(C=O)C>[CH2:18]([O:13][C:12]1[C:6]2[O:5][CH:4]([O:3][CH2:1][CH3:2])[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1)[CH:17]=[CH2:16]

参加物

6

反応物 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 134470632-Ethoxy-benzo[1,3]dioxol-4-ol

生成物 1

HCID 699337744-Allyloxy-2-ethoxy-1,3-benzodioxolane

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 37 (4.0 g, 22.0 mmol) in DMF (7 mL) was added dropwise over 5 min to a suspension of sodium hydride (1.32 g, 33.0 mmol 60% dispersion in oil) in DMF (15 mL) at 0° C. The reaction mixture was stirred at this temperature for 15 min, then allyl bromide (2.93 g, 2.09 mL, 24.2 mmol) was added and the reaction mixture was allowed to warm to rt over 16 h. The reaction mixture was then cooled to 0° C., water was added dropwise, then the reaction mixture was extracted with t-BuOMe (3×). The organic phase was washed successively with water and brine, dried (Na2SO4) and evaporated to dryness to give 4.8 g of crude product. Purification by column chromatography (SiO2 2:98 EtOAc:cyclohexane) gave 38 compound (3.3 g, 68%):

後処理

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. extractionthe reaction mixture was extracted with t-BuOMe (3×)
  3. washThe organic phase was washed successively with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customto give 4.8 g of crude product
  7. customPurification by column chromatography (SiO2 2:98 EtOAc:cyclohexane)

出典と根拠

ORDレコード
ord-2a25e37172664dd499c230b08964c9af
出典データセット
uspto-grants-2012_06
特許番号
US08198302B2

反応ノート

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