Sulfuric Acid → ethyl 6-chloro-7-[hydroxy(thien-2-yl)methyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854981Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]=[O:13])[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[Mg]Br.OS(O)(=O)=O>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([OH:13])[C:24]1[S:23][CH:27]=[CH:26][CH:25]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2

Participants

Conditions

Temperature: -30 °C

Procedure

The title product from Example 170 Step 1 (100 mg, 0.31 mmol) was dissolved in 1.0 mL of Et2O and cooled to −30° C. To this solution was added 0.31 mL thiophene-2-yl magnesium bromide solution (1.0 M in THF). After 10 minutes, the reaction mixture was pipetted over ice and diluted with ether and a dilute solution of H2SO4. The organic extracts were washed with a saturated solution of NaHCO3, dried over MgSO4, filtered, and evaporated under reduced pressure to dryness to provide 112 mg of a yellow oil. This oil was used as is without further purification.

Workup

washThe organic extracts were washed with a saturated solution of NaHCO3
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under reduced pressure to dryness

Sources & evidence

ORD record: ord-a9c6df2304dd452e961f8ea5466c4395
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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