Potassium Carbonate → ethyl 6-methoxy-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855100Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

The ethyl 6-hydroxy-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.2 g, 0.66 mmole) and K2CO3 (0.48 g, 3.44 mmole) was suspended in acetone (7.5 mL). lodomethane (0.93 g, 6.60 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 (0.22 g, 98%). GCMS m/z 316.0 (M+). LCMS m/z 317.0 (M+H). 1H NMR (CDCl3/400 MHz) 7.64 (s, 1H), 6.72 (s, 1H), 6.55 (s, 1H), 5.65 (q, 1H, J=7.0 Hz), 4.28 (m, 2H), 3.73 (s, 3H), 2.20 (s, 3H), 1.32 (m, 3H).

Workup

additionlodomethane (0.93 g, 6.60 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-ff26d5eb08164b18a03dcdffd223e0d8
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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