Hydrochloric Acid → 2-Propenoic acid, 3-(2-furanyl)-, 1-methylethyl ester

HRID 421292

반응식

HRID 421292 반응식
S(Cl)(Cl)=O.[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH:10]=[CH:11][C:12]([OH:14])=[O:13].[CH3:15][CH:16](O)[CH3:17].Cl>C(Cl)(Cl)Cl.CN(C=O)C>[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1/[CH:10]=[CH:11]/[C:12]([O:14][CH:16]([CH3:17])[CH3:15])=[O:13]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 10876Furylacrylic acidHCID 24386Thionyl Chloride

생성물 1

HCID 9099322-Propenoic acid, 3-(2-furanyl)-, 1-methylethyl ester수율 96%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

1.46 ml of thionyl chloride (20 mmol) were added to a solution of 1.38 g of 3-(2-furyl)acrylic acid (10 mmol) in 10 ml of chloroform and 0.1 ml of DMF. The solution was warmed to 70° C. and kept at this temperature for 1 h, then the solvents were removed under reduced pressure and the residue was dissolved in 6.6 ml of DCM and 3.3 ml of pyridine and subsequently cooled to 0° C. 0.96 ml of 2-propanol (12.5 mmol) was added, the temperature was increased to RT and the reaction mixture was stirred for 2.5 h. It was acidified with 30 ml of 1 M hydrochloric acid and extracted with 150 ml of ethyl acetate. The organic phase was washed with aqueous sodium hydrogencarbonate solution, dried over sodium sulfate, filtered and the solvents were removed under reduced pressure. 1.72 g (yield: 96%) of the title compound were obtained. LC/MS (Method D) (M+H-isopropyl)+ 139

후처리

  1. customthe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 6.6 ml of DCM
  3. temperature3.3 ml of pyridine and subsequently cooled to 0° C
  4. temperaturethe temperature was increased to RT
  5. extractionextracted with 150 ml of ethyl acetate
  6. washThe organic phase was washed with aqueous sodium hydrogencarbonate solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure

출처 및 근거

ORD 기록
ord-9be70656195b4bdda623c09e30b4d6b4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097758B2

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