Sodium hydride → HCID 54257849, compound

HRID 2225733Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5](=[O:15])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.CS(O[CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[C:27]([O:34][C:35](=[O:41])[C:36]([CH3:40])([CH3:39])[CH2:37][CH3:38])[CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=O)=O>CN(C)C=O.[Cl-].[Na+].O>[CH3:3][O:4][C:5](=[O:15])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:21][CH2:22][O:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[C:27]([O:34][C:35](=[O:41])[C:36]([CH3:39])([CH3:40])[CH2:37][CH3:38])[CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred suspension of sodium hydride (55% dispersion in mineral oil, 0.105 g) in dimethylformamide (5 mL) was added dropwise a solution of 4-hydroxy-alpha-oxobenzene acetic acid methyl ester (0.432 g) in dimethylformamide (5 mL) under argon. The mixture was then treated dropwise with a solution of 2-[8-(2,2-dimethyl-1-oxobutoxy)-2naphthalenyloxy]ethyl methanesulfonate (0.76 g) in dimethylformamide (5 mL). The reaction was heated for 18 hours at 60° C., diluted with brine, and extracted with ethyl acetate. After evaporation of volatiles, the residue was purified by chromatography over silica gel (hexane-ethyl acetate; 10: 1) to yield 0.375 g of 4-[[2-[8-(2,2-dimethyl-1-oxobutoxy)-2-naphthalenyloxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester as a white solid, mp 119°-120° C.

Workup

extractionextracted with ethyl acetate
customAfter evaporation of volatiles
customthe residue was purified by chromatography over silica gel (hexane-ethyl acetate; 10: 1)

Sources & evidence

ORD record: ord-053b793e90734a80b593e9d0c49a0521
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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