Triethylamine → HCID 15029658, compound

HRID 1607255Notes

Reaction equation

HRID 1607255 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

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 128132L 656224

Product 1

HCID 15029658HCID 15029658, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customThe volatiles were removed in vacuo
  2. customThe residue was purified by chromatography on silica gel
  3. washeluted with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-32c4c1400ab44a2c9bc9236ad88b5c40
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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