Dimethyl Sulfate → Methyl-7-cyclopentyloxy-2-methylbenzo[b]furan-4-carboxylate

HRID 548994Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

To a suspension of 7-cyclopentyloxy-2-methylbenzo[b]furan-4-carboxylic acid (40.0 g, 0.153 moles) and potassium carbonate (42.0 g, 0.184) in acetone (400 mL) added dimethyl sulfate (24.0 g, 0.307 moles) and refluxed for 4-5 hrs. acetone (305 mL) was distilled off and reaction mixture was cooled to 5° C., ice cold water (500 mL) was and the solid separated was filtered, washed with water (2×100 mL) and dried to get off white solid (43.0 g).

Workup

temperaturerefluxed for 4-5 hrs
distillationacetone (305 mL) was distilled off
customreaction mixture
customthe solid separated
filtrationwas filtered
washwashed with water (2×100 mL)
customdried

Sources & evidence

ORD record: ord-cc00225147134d58a0bd648533e81db4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943634B2

Reaction notes

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