Diglyme → 3,4-Dipropionyloxy-1-butene

HRID 54725

반응식

HRID 54725 반응식
[C:1]([O:5][C:6](=[O:9])[CH2:7][CH3:8])(=O)[CH2:2][CH3:3].C(N([CH2:15][CH3:16])CC)C.[O:17]1[CH2:21][CH:18]1C=C.C[O:23]CCOCCOC>>[C:6]([O:5][CH:1]([CH2:18][O:17][C:21](=[O:23])[CH2:15][CH3:16])[CH:2]=[CH2:3])(=[O:9])[CH2:7][CH3:8]

참가 물질

5

반응물 4

HCID 8150DiglymeHCID 8471TriethylamineHCID 13586VinyloxiraneHCID 31263Propionic anhydride

생성물 1

HCID 212251023,4-Dipropionyloxy-1-butene수율 84%

반응 조건

온도
125 °C

실험 절차

A 100-mL autoclave was charged with 57.2 g (0.44 mol) propionic anhydride, 1.62 g (0.016 mol) of triethylamine and 3.44 g of diglyme. The autoclave was purged with helium twice, then the vessel was pressurized to 6.2 bars (75 psig) with helium followed by agitation. The reaction mixture was heated to 125° C., then 31.35 mL (0.40 mol) of 3,4-epoxy-1-butene was introduced to the reactor via syringe pump over 10 seconds. A first sample was taken at 1 min, then sequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed an 84% yield of 3,4-dipropionyloxy-1-butene with a 94% selectivity and 11.2% 3,4-epoxy-1-butene. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant of 0.017 min-1 (Table A). This example shows the use of another carboxylic anhydride with triethylamine and no carboxylic acid co-catalyst.

후처리

  1. customThe autoclave was purged with helium twice
  2. customsequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC

출처 및 근거

ORD 기록
ord-8c0406fc12254a49995314db749bae9a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623086

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