Diethyl Oxalate → HCID 21110635, compound

HRID 1766685Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH3:22])[C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH3:20])[C:13]=2[CH3:21])=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.[C:23](OCC)(=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[CH2:19]([C:14]1[C:13]([CH3:21])=[C:12]([CH:17]=[CH:16][C:15]=1[OH:18])[O:11][C:5]1[C:4]([CH3:22])=[CH:3][C:2]([NH:1][C:23](=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2)[CH3:20]

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 23031084HCID 23031084, compound

Product 1

HCID 21110635HCID 21110635, compoundYield 93.5%

Conditions

Temperature: 120 °C

Procedure

To 4-(7-amino-5-methylindan-4-yloxy)-2-ethyl-3-methylphenol (12 mg) was added diethyl oxalate (150 mg), and the mixture was stirred under an argon atmosphere at 120° C. for 3 hours. The reaction mixture was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=2/1) to give the title compound (15 mg).

Workup

customThe reaction mixture was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-bfadfe816abe473fa75eb12b46690e87
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230031B2

Reaction notes

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