Pyridine → Chloromethyl 4-acryloyloxybutyl carbonate

HRID 260620

반응식

HRID 260620 반응식
N1C=CC=CC=1.Cl[C:8]([O:10][CH2:11][Cl:12])=[O:9].[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])(=[O:16])[CH:14]=[CH2:15]>ClCCl>[C:8](=[O:9])([O:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:14]=[CH2:15])[O:10][CH2:11][Cl:12]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 755884-Hydroxybutyl acrylate

생성물 1

HCID 54357452Chloromethyl 4-acryloyloxybutyl carbonate수율 74.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of chloromethyl chloroformate (0.98 ml, 11.00 mmol) and 4-hydroxybutyl acrylate (1.38 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00 M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 1.76 g (74%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4 H, m, CH2 --CH2), 4.27 (4 H, m, 2×CH2 --O), 5.77 (2 H, s, Cl--CH2 --O), 5.8-6.7 (3 H, m, CH=CH2).

후처리

  1. washThe reaction mixture is washed with hydrochloric acid (1.00 M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-67a0952df54046a3b95ef10ea3b9243a
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05529766

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