Potassium Carbonate → Methyl 7-(4-(tert-butoxycarbonyl)-2-methylphenoxy)-6-cyanochroman-4-carboxylate

HRID 1626400Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].[OH:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][C:20]=1[CH3:32].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:26]([O:25][C:23]([C:22]1[CH:30]=[CH:31][C:19]([O:18][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[C:20]([CH3:32])[CH:21]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 6-cyano-7-fluorochroman-4-carboxylate (0.200 g, 0.850 mmol), tert-butyl 4-hydroxy-3-methylbenzoate (0.195 g, 0.935 mmol) and potassium carbonate (0.141 g, 1.02 mmol) were dissolved in 4 mL of dry DMSO and degassed with argon. The solution was heated in a microwave oven at 150° C. for 15 minutes, then at 170° C. for 15 additional minutes. The reaction was poured into 10% HCl/water (1 L), extracted with ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to a yellow film. The crude product was adsorbed onto silica gel and purified by column using 20-30% ethyl acetate/hexanes to provide the desired product (0.133 g, 37%) as a light yellow foam.

Workup

customdegassed with argon
customat 170° C.
additionThe reaction was poured into 10% HCl/water (1 L)
extractionextracted with ethyl acetate
washthe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to a yellow film
custompurified by column

Sources & evidence

ORD record: ord-d27d18b7388349b58e071dcbdaf22ffe
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

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