Ethanol → Methyl 3-(4-((2'-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422288

Reaction equation

HRID 2422288 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1.[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(O)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)[CH:3]=1)[CH3:23]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2734902(2-Ethoxyphenyl)boronic acidHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

Product 1

HCID 23083192Methyl 3-(4-((2'-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoateYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-[4-[(3-bromobenzyl)oxy]phenyl]propanoate (0.30 g, 0.86 mmol), 2-ethoxyphenylboronic acid (0.16 g, 0.95 mmol), tetrakistriphenylphosphine palladium (40 mg, 0.034 mmol), 2N potassium carbonate aqueous solution (0.3 mL), ethanol (0.3 mL) and toluene (3 mL) was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give methyl 3-(4-((2′-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate (0.21 g, 63%) as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

Sources & evidence

ORD record
ord-a3f0659dc5fd4a16ba8c2dbd58ae8010
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Linked notes

Loading…