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

HRID 218264노트

반응식

HRID 218264 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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%):

후처리

  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)

출처 및 근거

ORD 기록
ord-2a25e37172664dd499c230b08964c9af
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198302B2

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