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

HRID 1392693Notes

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-71446101ae344c398eac05bafc16b232
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342024B2

Reaction notes

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