1,5-Diazabicyclo(4.3.0)non-5-ene → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

HRID 1763955

반응식

HRID 1763955 반응식
[CH3:1][C:2]1([CH3:19])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[C:3]1(C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].N12CCCC1=NCCC2>CC1C=CC=CC=1C>[CH2:12]([O:11][C:9]([CH:3]1[CH:4]([CH:5]=[C:6]([Cl:7])[Cl:8])[C:2]1([CH3:1])[CH3:19])=[O:10])[CH3:13]

참가 물질

4

반응물 2

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 14914133Ethyl 2-(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropanecarboxylate

생성물 1

HCID 101094Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester수율 47.1%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

13 g of diethyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1,1-dicarboxylate were dissolved in 50 g of o-xylene and 20 g of 1,5-diaza-bicyclo[4.3.0]non-5-ene were added. The mixture was then heated to the boil for 8 hours. After cooling, ice-cold dilute hydrochloric acid was added, so that a neutral or weakly acid pH value resulted. The organic phase was separated off and dried with Na2SO4 and the xylene was distilled off in vacuo (boiling point = 35° - 40° C./12 mm Hg). The residue weighed 12.5 g. Fractional distillation gave 4.7 g of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropane-1-carboxylic acid ethyl ester, of which 30% was in the cis form and 70% was in the trans form. The boiling point was 65° - 72° C./0.3 mm Hg. The nuclear magnetic resonance spectrum agreed with that given in the literature. 6.5 g of the starting material were recovered. The yield was thus 92%.

후처리

  1. temperatureThe mixture was then heated to the boil for 8 hours
  2. temperatureAfter cooling
  3. additionice-cold dilute hydrochloric acid was added
  4. customresulted
  5. customThe organic phase was separated off
  6. dry with materialdried with Na2SO4
  7. distillationthe xylene was distilled off in vacuo (boiling point = 35° - 40° C./12 mm Hg)
  8. distillationFractional distillation

출처 및 근거

ORD 기록
ord-78e28cdd9aae484aba09ec936786bc3d
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04113969

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