Water → Ethyl 5-(hydroxy(phenyl)methyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845258Notes

Reaction equation

HRID 1845258 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([C:11]1[CH:12]=[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:16]=1)=[O:10].O>O1CCCC1>[OH:10][CH:9]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]1[CH:12]=[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 58188063Ethyl 5-formyl-4'-methylbiphenyl-3-carboxylateHCID 178418255HCID 178418255, compound

Product 1

HCID 58188027Ethyl 5-(hydroxy(phenyl)methyl)-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenylmagnesium bromide (850 mg, 4.7 mmol) was added to a solution of ethyl 5-formyl-4′-methylbiphenyl-3-carboxylate (360 mg, 1.3 mmol) in tetrahydrofuran (8 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 h, and then water (10 mL) was added. The mixture was extracted with EtOAc (20 mL×2). The combined organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel column chromatography to afford the title compound.

Workup

  1. extractionThe mixture was extracted with EtOAc (20 mL×2)
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0503f22ad9bb48d7bc8db8ce8dadf627
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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