Hydrochloric Acid → 2-(trans)-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic Acid

HRID 1294362Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ester from step 2 and NaOH (20%, 30 mL) was heated to 100° C. for 1.5 h, cooled to rt, acidified with HCl 10% and extracted with EtOAc. The organic extract was dried over Na2SO4 and the solvent evaporated to afford the title compound.

Workup

temperaturecooled to rt
extractionextracted with EtOAc
extractionThe organic extract
dry with materialwas dried over Na2SO4
customthe solvent evaporated

Sources & evidence

ORD record: ord-d15eab87939f488b96d245097202188f
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238706B2

Reaction notes

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