Water → ethyl 8-chloro-6-ethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854990노트

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HRID 854990 반응식
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:28](B(CC)CC)[CH3:29].O>CN(C=O)C.C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:28][CH3:29])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2

참가 물질

8

반응물 4

HCID 962WaterHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 58934641ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 69516448ethyl 8-chloro-6-ethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
110 °C

실험 절차

To a solution of 500 mg (1.16 mmol) ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 3 mL of anhydrous DMF was added 0.481 g (3.48 mmol, 3.0 eq.) of potassium carbonate, 0.134 g (0.116 mmol, 0.1 eq.) of tetrakis(triphenylphosphine)-palladium(0) and 1.74 mL (1.74 mmol, 1.5 eq.) of 1M triethylborane in THF. The vessel was heated to 110° C. for 5 hours under a nitrogen atmosphere. After cooling to room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic layer was washed 4 times with water and 2 times with brine, dried over sodium sulfate, filtered and concd in vacuo. The product was carried to the next step without further purification.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed 4 times with water and 2 times with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe product was carried to the next step without further purification

출처 및 근거

ORD 기록
ord-35a02430a678469aa529f4c8dd031065
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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