Potassium Carbonate → ethyl 6-chloro-5,7-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854949

반응식

HRID 854949 반응식
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:7]([OH:11])=[CH:8][C:9]=1[CH3:10])[CH:5]=O.C([O-])([O-])=O.[K+].[K+].[F:19][C:20]([F:29])([F:28])/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]2[C:7](=[CH:8][C:9]=1[CH3:10])[O:11][CH:21]([C:20]([F:19])([F:29])[F:28])[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 33350823-Chloro-6-hydroxy-2,4-dimethylbenzaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

생성물 1

HCID 69339659ethyl 6-chloro-5,7-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate수율 110.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

To a solution of 3-chloro-6-hydroxy-2,4-dimethylbenzaldehyde (6.9 g, 37.4 mmol) in 80 mL of DMF was added dried finely powdered K2CO3 (11.36 g, 82.2 mmol). With mechanical stirring, the reaction was heated to 65° C. To the suspension was added dropwise ethyl trifluorocrotonate (7.54 g, 44.9 mmol). The stirring reaction was heated at 90° C. for 1.5 h. K2CO3 was filtered from the cooled reaction. From the reaction under vacuum, DMF was removed. The resulting residue was dissolved in 400 mL EtOAc. The organic solution was washed with 100 mL 1 M KHSO4, 70 mL of satd. KHCO3, 100 mL brine, followed by drying over MgSO4, and concentrating under vacuum. The crude desired product (13.8 g) of was isolated. After employing flash chromatography conditions, pure compound (9.8 g, 78%) of was isolated and its structure confirmed by NMR and LC-MS.

후처리

  1. customThe stirring reaction
  2. temperaturewas heated at 90° C. for 1.5 h
  3. filtrationK2CO3 was filtered from the cooled reaction
  4. customFrom the reaction under vacuum, DMF
  5. customwas removed
  6. dissolutionThe resulting residue was dissolved in 400 mL EtOAc
  7. washThe organic solution was washed with 100 mL 1 M KHSO4, 70 mL of satd
  8. dry with materialby drying over MgSO4
  9. concentrationconcentrating under vacuum

출처 및 근거

ORD 기록
ord-42540ae1ea6d43768d62b998090f1aae
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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