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

HRID 2205460Notes

Reaction equation

HRID 2205460 reaction equation
[OH:1][C:2]1[C:9]([I:10])=[CH:8][C:7]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:6][C:3]=1[CH:4]=O.C(N(CC)CC)C.[F:23][C:24]([F:33])([F:32])/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C=O)C>[I:10][C:9]1[CH:8]=[C:7]([O:11][C:12]([F:15])([F:14])[F:13])[CH:6]=[C:3]2[C:2]=1[O:1][CH:25]([C:24]([F:23])([F:33])[F:32])[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:4]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoateHCID 86599455HCID 86599455, compound

Product 1

HCID 86599457ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

The resulting product (2.5 g, 7.5 mmol) from step 1, triethylamine (2 mL) and ethyl 4,4,4-trifluorocrotonate (5.1 g, 30 mmol) were mixed in DMF (10 mL), and then the system was heated to 85° C. for reaction for 48 hrs. At the end of reaction, the reaction system was cooled to room temperature, added with water and extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.5 g of the product (69%) by column chromatography.

Workup

  1. customAt the end of reaction
  2. temperaturethe reaction system was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. customthe organic phase was dried
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-a6aa7b8364644478a8dc5871acae40f6
Source dataset
uspto-grants-2016_06
Patent number
US09371305B2

Reaction notes

Loading…