Hydrochloric Acid → Ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]acrylate

HRID 1826091노트

반응식

HRID 1826091 반응식
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][C:18](C)([O-])C.[K+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31]C(C=O)=[CH:27][C:26]=1[O:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=1.Cl>O1CCCC1>[CH2:17]([C:3](=[CH:2][C:1]1[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[C:26]([O:33][CH2:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:40][CH:41]=2)[CH:27]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:18]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 118094914-Methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]benzaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 58634019Ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]acrylate수율 99.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Under an argon atmosphere, stirring and cooling with ice, a solution of triethyl 2-phosphonobutyrate (555 mg, 2.20 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise to a solution of potassium tert-butoxide (250 mg, 2.23 mmol) in anhydrous tetrahydrofuran (10 mL), and then the mixture was stirred for 20 minutes. Following this, a solution of 4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]benzaldehyde (650 mg, 2.00 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise and then the mixture was stirred for 1 hour under cooling with ice and for 4 hours at room temperature. Cooled 0.5 mol/L hydrochloric acid (30 mL) was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=6:1 v/v) to afford 842 mg (99%) of the title compound as a colorless oily product.

후처리

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred for 20 minutes
  3. additionwas added dropwise
  4. stirringthe mixture was stirred for 1 hour
  5. additionwas added to the reaction mixture, which
  6. extractionwas extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=6:1 v/v)

출처 및 근거

ORD 기록
ord-1d20cabc9b4046bd89a4a277f33fad00
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049342B2

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