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

HRID 421292

反応式

HRID 421292 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-9be70656195b4bdda623c09e30b4d6b4
出典データセット
uspto-grants-2012_01
特許番号
US08097758B2

関連ノート

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