Sodium hydride → 4-(4-(benzyloxy)phenyl)-3-(4-methoxyphenyl)furan-2(5H)-one

HRID 446810Notes

Reaction equation

HRID 446810 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=O)=[O:11])=[CH:5][CH:4]=1.[H-].[Na+]>CN(C=O)C>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[CH2:13][O:12][C:10](=[O:11])[C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][CH:18]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 583680092-(4-(Benzyloxy)phenyl)-2-oxoethyl 2-(4-methoxyphenyl)acetate

Product 1

HCID 670755844-(4-(benzyloxy)phenyl)-3-(4-methoxyphenyl)furan-2(5H)-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 2-(4-(benzyloxy)phenyl)-2-oxo-ethyl 2-(4-methoxyphenyl)acetate (3.0 g, 0.007 mol) in DMF (20 mL) was added NaH (0.96 g, 0.01 mol). The reaction mixture was stirred at RT for 30 minutes and quenched with ice to obtain a solid precipitate. The solid precipitate was filtered and dried in vacuo to afford 4-(4-(benzyloxy)phenyl)-3-(4-methoxyphenyl)furan-2(5H)-one (2.4 g, 84%) as a solid.

Workup

  1. customquenched with ice
  2. customto obtain a solid precipitate
  3. filtrationThe solid precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c7ecbe428441455a9419faf676c6e9c8
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

Loading…