Sodium hydride → HCID 19004275, compound

HRID 2225703Notes

Reaction equation

HRID 2225703 reaction equation
C[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+].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[C:27]12([O:37][CH2:38][CH2:39]O)[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2>CN(C)C=O>[O:12]=[C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:39][CH2:38][O:37][C:27]23[CH2:36][CH:31]4[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]4)[CH2:28]2)[CH2:34]3)=[CH:7][CH:6]=1)[C:3]([OH:2])=[O:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 2133291HCID 2133291, compoundHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 19004275HCID 19004275, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with the tosylate prepared from 2-(1-adamantyloxy) ethanol (1.5 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane-ethyl acetate; 80:20:2) and crystallized from diethyl ether-hexane to provide 0.77 g of alpha-oxo-4-[[2-[tricyclo(3.3.1.1-3,7)dec-1-yloxy]ethyl]oxy]benzeneacetic acid, mp 107°-109° C.

Workup

  1. extractionThe material from dichloromethane extraction
  2. customwas purified by HPLC (dichloromethane-hexane-ethyl acetate; 80:20:2)
  3. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-6ea1214b1a7f491bb8bd1254ffc8c2eb
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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