Sodium hydride → 4-[6-[2,3-Bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid ethyl ester

HRID 2225821Notes

Reaction equation

HRID 2225821 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].[C:17]1([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]Br)[C:26]=2[O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH2:23][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:26]=2[O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzene

Product 1

HCID 544397754-[6-[2,3-Bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid ethyl esterYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.97 g) in dimethylformamide (12 mL) was treated with 55% sodium hydride (0.22 g), stirred for 15 minutes and then 1,2-bis-(phenylmethoxy)-3-(6-bromohexyl)benzene (2.27 g) was added and rinsed in with dimethylformamide (3 mL). The mixture was stirred overnight at room temperature and worked up as in Example 20. The residual oil was purified by HPLC (ethyl acetate-hexane; 1:9) and crystallized from diethyl ether-hexane to provide 1.7 g of 4-[6-[2,3-bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 39°-42° C.

Workup

  1. washrinsed in with dimethylformamide (3 mL)
  2. stirringThe mixture was stirred overnight at room temperature
  3. customThe residual oil was purified by HPLC (ethyl acetate-hexane; 1:9)
  4. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-c6af5f9cb90f492b95ae3c227119695d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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