Potassium Carbonate → HCID 69517211, compound

HRID 855106Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=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.[C:23]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:23][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:15])[F:16])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2

Participants

Conditions

Temperature: 55 °C

Procedure

The ethyl 6-hydroxy-8-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.1 g, 0.31 mmole) and K2CO3 (0.23 g, 1.64 mmole) was suspended in acetone (5.0 mL). lodomethane (0.44 g, 3.1 mmole) was added and heated to 55 ° C. for 3 hrs. The contents were filtered through a plug of celite and washed with acetone. The solution was concentrated in vacuo to give a yellow solid (0.05 g, 50%). GCMS m/z 332.0 (M+). LCMS m/z 333.0 (M+H). 1H NMR (CDCl3/400 MHz) 7.64 (s, 1H), 6.54 (s, 1H), 6.32 (s, 1H), 5.68 (q, 1H, J=7.0 Hz), 4.28 (m, 2H), 3.85 (s, 3H), 3.75 (s, 3H), 1.32 (m, 3H).

Workup

additionlodomethane (0.44 g, 3.1 mmole) was added
filtrationThe contents were filtered through a plug of celite
washwashed with acetone
concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-a8914c4ba9204fd0979ea0e55a362f0d
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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