Sodium hydride → HCID 67830530, compound

HRID 2225834Notes

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]([O:31][CH3:32])[C:23]=1[CH2:33][CH2:34][CH3:35]>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]([O:31][CH3:32])[C:23]=2[CH2:33][CH2:34][CH3:35])=[CH:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.471 g) in dimethylformamide (10 mL) was treated with 55% sodium hydride (0.117 g), stirred for 15 minutes and then a solution of with 1-[4-(3-bromopropoxy)-2-methoxy-3propylphenyl]ethanone (0.8 g) in dimethylformamide (5 mL) was added. The mixture was heated at 50° C. for 17 hours and worked up as in Example 20. The residual oil was purified by HPLC (ethyl acetate-hexane; 1:4), followed by flash chromatography over silica gel (ethyl acetate-toluene; 1:19) to yield 0.4 g of 4-[3-[4-acetyl-3-methoxy-2-propylphenoxy)propoxy]-alpha-oxobenzeneacetic acid ethyl ester as an oil.

Workup

customThe residual oil was purified by HPLC (ethyl acetate-hexane; 1:4)

Sources & evidence

ORD record: ord-1fe495cb8fb64c52a675f7a10dc500e3
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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