Isobutyric Acid → Ethyl 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate

HRID 3016

반응식

HRID 3016 반응식
[C:1]([O:9]CC)([O:6][CH2:7][CH3:8])(OCC)[CH3:2].[Cl:12][C:13]([Cl:24])([C:20]([F:23])([F:22])[F:21])[CH:14](O)[CH:15]=[C:16]([CH3:18])[CH3:17].C(O)(=O)C(C)C>>[Cl:12][C:13]([Cl:24])([C:20]([F:21])([F:22])[F:23])[CH:14]=[CH:15][C:16]([CH3:18])([CH3:17])[CH2:2][C:1]([O:6][CH2:7][CH3:8])=[O:9]

참가 물질

4

반응물 3

HCID 6590Isobutyric AcidHCID 66221Triethyl orthoacetateHCID 136022405,5-Dichloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene

생성물 1

HCID 53946683Ethyl 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate

실험 절차

A mixture of triethyl orthoacetate (25 ml), 5,5-dichloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (3.5 g), and isobutyric acid (0.11 g) was heated at the reflux temperature. The refluxing volatiles were condensed and collected in a Dean & Stark apparatus containing molecular sieves (4A) to collect the by-product ethanol and separate it from the orthoacetate which was returned to the mixture. After 30 minutes the more volatile components were removed by evaporation under reduced pressure and the residual oil (consisting principally of 5,5-dichloro-4-(1,1-diethoxyethoxy)-2-methyl-6,6,6-trifluorohex-2-ene, 3.8 g) collected. This was then heated with isobutyric acid (10 μl) at the reflux temperature for 16 hours under a condenser containing molecular sieves (4A) to remove ethanol from the condensate. The residual oil was subjected to purification by column chromatography using a 15:1 (by volume) mixture of hexane:ethyl acetate as eluant and a silica gel column (230-400 mesh, 60 Å) to obtain ethyl 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate, identified by nuclear magnetic resonance, and gas chromatographic mass-spectroscopy.

후처리

  1. temperaturewas heated at the reflux temperature
  2. customcondensed
  3. customcollected in a Dean & Stark apparatus
  4. additioncontaining molecular sieves (4A)
  5. customto collect the by-product ethanol
  6. customseparate it from the orthoacetate which
  7. customAfter 30 minutes the more volatile components were removed by evaporation under reduced pressure
  8. customcollected
  9. temperatureThis was then heated with isobutyric acid (10 μl) at the reflux temperature for 16 hours under a condenser
  10. additioncontaining molecular sieves (4A)
  11. customto remove ethanol from the condensate
  12. customThe residual oil was subjected to purification by column chromatography
  13. additiona 15:1 (by volume) mixture of hexane

출처 및 근거

ORD 기록
ord-4d77e42f5c494f69b479d484b8ed6d48
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731475

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