Potassium Carbonate → Isohexane ethyl acetate

HRID 1767212Notes

Reaction equation

HRID 1767212 reaction equation
NC1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.[C:15](=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1>[CH3:15][CH2:11][O:10][C:8]([CH3:6])=[O:9].[CH3:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 2737799(3-Amino-5-(methoxycarbonyl)phenyl)boronic acid

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 882672-Methylphenethyl alcoholSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-amino-5-methoxycarbonylphenylboronic acid (161 mg, 0.82 mmol), Pd(0) [PPh3]4 (50 mg, 5 mol %), potassium carbonate (905 mg, 6.6 mmol) and 2-(2-benzyloxy-5-chloro)phenyl-1-bromocyclopent-1-ene (298 mg, 0.82 mmol) in toluene-ethanol (1:1 10 mL) were stirred at 90° C., under nitrogen, for 2 hrs. After cooling the reaction mixture was poured onto water (10 ml) and extracted with diethyl ether (2×10 ml). The combined extracts were dried and evaporated. Flash chromatography [EtOAc/Iso-hexane 5:95-1:4] gave the product as a yellow oil 200 mg 56% LC/MS: Rt=4.00 [M+H] 434 (1 Cl)

Workup

  1. temperatureAfter cooling the reaction mixture
  2. additionwas poured onto water (10 ml)
  3. extractionextracted with diethyl ether (2×10 ml)
  4. customThe combined extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-68ffa633470f43cc820eaf9a35d52571
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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