Sodium hydride → HCID 54143518, compound

HRID 2225819Notes

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+].Br[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=1[CH2:32][CH2:33][CH3:34]>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][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=2[CH2:32][CH2:33][CH3:34])=[CH:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.776 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and then 1-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl] ethanone (1.26 g) was added and rinsed in with a little dimethylformamide. The mixture was heated at 50° C. for 6 hours and worked up as in Example 20. The crude material was purified by HPLC (ethyl acetate-hexane; 1:4) to furnish 0.7 g of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester as an oil.

Workup

washrinsed in with a little dimethylformamide
customThe crude material was purified by HPLC (ethyl acetate-hexane; 1:4)

Sources & evidence

ORD record: ord-a91f9680931e4f5da240b485fa92643c
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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