Water → ethyl 7-tert-butyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855104Notes

Reaction equation

HRID 855104 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][C:6]=1Cl)([CH3:4])([CH3:3])[CH3:2].[C:25]([O-])([O-])=O.[Cs+].[Cs+].CB1OB(C)OB(C)O1.O>COCCOCCOC>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][C:6]=1[CH3:25])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 21883510ethyl 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517309ethyl 7-tert-butyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 38.2%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
115 °C

Procedure

The ethyl 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 8, Step 2 (1 g, 2.75 mmole) was dissolved in diglyme (20 mL). Cs2CO3 (1.5 g, 3.07 mmole), trimethylboroxaine (0.75 mL, 5.36 mmole), and [(t-Bu3P)PdBr]2 (20 mg) were added to above solution. The mixture was heated to 115° C. for 15 hrs under nitrogen. LCMS indicated that there was 50% conversion. The reaction was cooled down and the water was added to quench the reaction. The product was extracted with EtOAc and washed with water. The crude mixture was purified by RPHPLC to give the desired product 360 mg as an oil (38% yield), which had suitable purity to use without further purification.

Workup

  1. temperatureThe reaction was cooled down
  2. customto quench
  3. customthe reaction
  4. extractionThe product was extracted with EtOAc
  5. washwashed with water
  6. customThe crude mixture was purified by RPHPLC

Sources & evidence

ORD record
ord-46b63fee7f2142b29baa42b9eb0f4c3e
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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