Triethylamine → HCID 15029658, compound

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17]([Cl:18])=[CH:16][C:15]([CH2:19][CH2:20][CH3:21])=[C:14]([OH:22])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.ClC(OCC)=O.C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[O:22][C:14]3[C:15]([CH2:19][CH2:20][CH3:21])=[CH:16][C:17]([Cl:18])=[C:10]([OH:9])[C:11]=3[C:12]=2[CH3:13])=[CH:23][CH:24]=1

Participants

Procedure

A solution of 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (0.10 gm, 0.29 mmoles), ethyl chloroformate (0.1 mL) and triethylamine (1.0 mL) in tetrahydrofuran (15 mL) was stirred at room temperature overnight. The volatiles were removed in vacuo. The residue was purified by chromatography on silica gel and eluted with 15% ethylacetate in hexane to yield 100 mg (91%) of 2 (p-methoxybenzyl) 3 methyl 4 ethoxycarbonyloxy 5 -5-propyl 7 chlorobenzofuran, mp. 99°-100° C.