Hydrochloric Acid → 3-(1-Carboxy-cyclopentyl)-phenylboronic acid

HRID 216219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216219
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:13]2([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.[B:21](OCCCC)([O:27]CCCC)[O:22]CCCC.Cl>C1COCC1.O>[C:18]([C:13]1([C:9]2[CH:8]=[C:7]([B:21]([OH:27])[OH:22])[CH:12]=[CH:11][CH:10]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1)([OH:20])=[O:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 12712Tributyl borateHCID 157427251-(3-Bromophenyl)cyclopentane-1-carboxylic acidHCID 178418339Butyllithium

Produkt 1

HCID 690700543-(1-Carboxy-cyclopentyl)-phenylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of n-butyl lithium (2.5 M in hexanes, 5 mL, 12.48 mmol) in THF (30 mL) is chilled to −78° C., and a solution of 1-(3-bromo-phenyl)-cyclopentanecarboxylic acid [1.05 g, 3.9 mmol] in THF (10 mL) is added dropwise via syringe. The solution is stirred at temperature for 45 minutes and treated with tributyl borate (3.2 mL, 11.7 mmol). The reaction mixture is allowed to stir for 2.5 hours and then diluted with water (60 mL), acidified with 3M HCl and extracted twice with EtOAc (50 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 3-(1-carboxy-cyclopentyl)-phenylboronic acid as a solid, which is used without further purification.

Aufarbeitung

  1. stirringto stir for 2.5 hours
  2. extractionextracted twice with EtOAc (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6f7e39962dd1458898dbeb574e94c688
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193183B2

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