Hydrochloric Acid → 3-(2,3-Dihydro-1-benzofuran-7-yl)-3-methylbutanoic acid

HRID 916044Notes

Reaction equation

[O:1]1[C:5]2[C:6]([C:10]([CH3:19])([CH3:18])[CH2:11][C:12](=[O:17])C(F)(F)F)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[OH-:20].[Na+].Cl>C(OCC)(=O)C>[O:1]1[C:5]2[C:6]([C:10]([CH3:19])([CH3:18])[CH2:11][C:12]([OH:17])=[O:20])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(2,3-Dihydrobenzofur-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanone (1.00 g) was treated with NaOH (3.6 mL, 4 M in ethanol-water (2:1)) at room temperature. The mixture was heated to 80° C. for 1 hour. After the mixture had been cooled to room temperature, 20 mL of ethyl acetate, and approximately 15 mL of 2 M HCl were added. The organic phase was separated and the aqueous layer was extracted with three 20 mL portions of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed to yield 800 mg (99%) of 3-(2,3-dihydrobenzofur-7-yl)-3-methylbutanoic acid as an orange-brown solid.

Workup

temperatureAfter the mixture had been cooled to room temperature
customThe organic phase was separated
extractionthe aqueous layer was extracted with three 20 mL portions of ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulfate
customThe solvent was removed

Sources & evidence

ORD record: ord-5a60ab55f63f4f6797f9db83a417b27a
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268152B2

Reaction notes

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