Dimethylformamide dimethyl acetal → Ethyl 3-(dimethylamino)-2-{2-[(4-methoxyphenyl)methyl]-2H-tetrazol-5-yl}prop-2-enoate

HRID 1828449Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][O:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2[N:20]=[N:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:17]2)=[CH:13][CH:12]=1>>[CH3:6][N:4]([CH3:5])[CH:3]=[C:21]([C:18]1[N:19]=[N:20][N:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:28][CH:27]=2)[N:17]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal

HCID 15090418HCID 15090418, compound

Product 1

HCID 53425728Ethyl 3-(dimethylamino)-2-{2-[(4-methoxyphenyl)methyl]-2H-tetrazol-5-yl}prop-2-enoateYield 48%

Conditions

Temperature: 100 °C

Procedure

Dimethylformamide dimethylacetal (13 ml, 97.3 mmol) was dissolved in ethyl 2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]acetate (24 g, 88.4 mmol) and heated to 100° C. for 3 hours with stirring. The reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1→1:3) to obtain 14 g (48%) of yellow crystals.

Workup

customThe reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1→1:3)

Sources & evidence

ORD record: ord-dc7bdf859c044299b936d4b30b00d86b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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