Sodium hydride → HCID 53866524, compound

HRID 2225750Notes

Reaction equation

HRID 2225750 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 53866524HCID 53866524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.50 g in 5 mL of dimethylformamide was treated with 60% sodium hydride (0.112 g) and after 15 minutes, 2-bromomethylnaphthalene (0.61 g) was added. The reaction mixture was stirred 45 minutes at room temperature, was quenched with 0.1 mL of acetic acid and was diluted with diethyl ether-ethyl acetate (10: 1, 50 mL). The mixture was washed with water (2×10 mL) and brine (1×10 mL), dried (1MgSO4) and chromatographed over 100 g of silica gel eluting with dichloromethane-hexane (1:1) to give 0.61 g of 4-[(2-naphthalenyl)methoxy]alpha-oxobenzeneacetic acid methyl ester, mp 101°-102° C.

Workup

  1. customwas quenched with 0.1 mL of acetic acid
  2. additionwas diluted with diethyl ether-ethyl acetate (10: 1, 50 mL)
  3. washThe mixture was washed with water (2×10 mL) and brine (1×10 mL)
  4. customdried (1MgSO4)
  5. customchromatographed over 100 g of silica gel eluting with dichloromethane-hexane (1:1)

Sources & evidence

ORD record
ord-2e5e1dac7d1741c8b20b3eb73da8c3c3
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…