Methyl 4-Formylbenzoate → Methyl 4-[(RS)-hydroxy(6-methoxy-2-naphthyl)methyl]benzoate

HRID 545451Notes

Reaction equation

HRID 545451 reaction equation
[Li]CCCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13](Br)[CH:12]=[CH:11]2.[CH:19]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)=[O:20].[Cl-].[NH4+]>C1COCC1.C(=O)=O.CC(C)=O.CCOC(C)=O>[OH:20][CH:19]([C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:7][CH3:6])[CH:9]=2)[CH:14]=1)[C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 15294Methyl 4-FormylbenzoateHCID 25517Ammonium ChlorideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418339Butyllithium

Product 1

HCID 67203038Methyl 4-[(RS)-hydroxy(6-methoxy-2-naphthyl)methyl]benzoate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 18522661Acetone cardiceSolvent2×

Procedure

n-BuLi (4.4 mL of a 2.5 M solution in hexanes, 11 mmol) was added dropwise to a solution of 6-methoxy-2-bromonaphthalene (2.4 g, 10 mmol) in 80 mL of THF cooled in dry ice-acetone bath. After aging for 15 min, the cold mixture was quickly cannulated to a stirring mixture of methyl 4-formylbenzoate (1.64 g, 10 mmol) in 20 mL of THF cooled in dry ice-acetone bath. After stirring for an additional 15 min, the reaction mixture was poured into a mixture of aq ammonium chloride, hexanes and EtOAc. The organic phase was separated, concentrated and purified by flash chromatography on silica gel (mobile phase=10% to 30% EtOAc in hexanes) to give the title compound as a racemic mixture.

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel (mobile phase=10% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a72b9ad5fae94b0b96692105e84e7269
Source dataset
uspto-grants-2011_05
Patent number
US07935713B2

Reaction notes

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