Potassium acrylate → Acryloyloxymethyl 4-acryloyloxybutyl carbonate

HRID 260623

반응식

HRID 260623 반응식
[C:1](=[O:15])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:14])[CH:12]=[CH2:13])[O:2][CH2:3]Cl.[C:16]([O-:20])(=[O:19])[CH:17]=[CH2:18].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1](=[O:15])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:14])[CH:12]=[CH2:13])[O:2][CH2:3][O:20][C:16](=[O:19])[CH:17]=[CH2:18]

참가 물질

5

반응물 2

HCID 4429391Potassium acrylateHCID 54357452Chloromethyl 4-acryloyloxybutyl carbonate

생성물 1

HCID 54145101Acryloyloxymethyl 4-acryloyloxybutyl carbonate수율 91.1%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6228Dimethylformamide용매

실험 절차

Chloromethyl 4-acryloyloxybutyl carbonate (1.183 g, 5.00 mmol) prepared as described in Preparation 9 is added to a suspension of freeze dried potassium acrylate (0.606 g, 5.50 mmol) and 18-crown-6 (0.066 g, 0.25 mmol) in dimethylformamide (50 ml) under a dry N2 atmosphere. After 5 days at 20° C. the solvent is removed under reduced pressure and the residue dissolved by adding dichloromethane (60 ml) and water (30 ml). After separating the phases the aqueous layer is extracted with dichloromethane (3×30 ml) and the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.24 g (91%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4 H, m, CH2 --CH2), 4.23 (4 H, m, 2× CH2 --O), 5.88 (2 H, s, O--CH2 --O), 5.7-6.8 (6 H, 2×CH=CH2).

후처리

  1. customas described in Preparation 9
  2. customAfter 5 days at 20° C. the solvent is removed under reduced pressure
  3. dissolutionthe residue dissolved
  4. additionby adding dichloromethane (60 ml) and water (30 ml)
  5. customAfter separating the phases the aqueous layer
  6. extractionis extracted with dichloromethane (3×30 ml)
  7. washthe combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  8. dry with materialThe organic phase is dried (MgSO4)
  9. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-e4fdaf1f2a6947a299651ebe29481173
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05529766

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