Lithium Hydroxide → 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic acid

HRID 1392712Notes

Reaction equation

HRID 1392712 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]([CH:15]3[CH2:17][CH:16]3[C:18]([O:20]CC)=[O:19])=[CH:11][CH:10]=2)[O:3]1.[Li+].[OH-]>C1COCC1.O>[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]([CH:15]3[CH2:17][CH:16]3[C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)[O:5]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66579675Ethyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylate

Product 1

HCID 691581982-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ester from step 2 in THF-H2O (0.2M) was added LiOH (3 eq, 2M) and the mixture was stirred at rt for 18 h. The organic solvent evaporated, aqueous was acidified with HCl 1N and the acid extracted with EtOAc (3×). The organic was washed with brine, dried and solvent evaporated to afford the title carboxylic acid.

Workup

  1. customThe organic solvent evaporated
  2. extractionthe acid extracted with EtOAc (3×)
  3. washThe organic was washed with brine
  4. customdried
  5. customsolvent evaporated

Sources & evidence

ORD record
ord-ed74b980dbf2423da1a7b22d328f4b43
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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