Sodium Hydroxide → 4-(4-Boronophenyl)butanoic acid

HRID 735495Notes

Reaction equation

HRID 735495 reaction equation
CC1(C)C[O:6][B:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)[O:4]C1.[OH-].[Na+]>C(OCC)C>[B:5]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:13]=1)([OH:6])[OH:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578427774-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acid

Product 1

HCID 578425984-(4-Boronophenyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2A (343 mg, 1.24 mmol) was added to a mixture of diethyl ether (10 mL) and NaOH (2 mL, 2 N). The reaction mixture was stirred at rt for 10 min. The ether layer was separated and then treated with an additional portion of NaOH for 5 min. The combined aqueous layers were washed with diethyl ether (2×) and acidified to pH 4 with hydrochloric acid (6 N). The resulting solid precipitate was collected by filtration to afford 2B contaminated with 2A (212 mg, 1:1 2B/2A, 43% yield based on content of 2B) as a beige solid.

Workup

  1. customThe ether layer was separated
  2. additiontreated with an additional portion of NaOH for 5 min
  3. washThe combined aqueous layers were washed with diethyl ether (2×)
  4. filtrationThe resulting solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-8d13820ec3e0417f908214fdc9e1207f
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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