Acetic Anhydride → HCID 14579783, compound

HRID 1607253Notes

Reaction equation

HRID 1607253 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH2:20][CH3:21])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].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:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][C:24](=[O:26])[CH3:25])=[C:14]([CH2:19][CH2:20][CH3:21])[C:11]=3[C:12]=2[CH3:13])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14579778HCID 14579778, compound

Product 1

HCID 14579783HCID 14579783, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(p-methoxybenzyl)-3-methyl-4-propyl-5-hydroxy-benzofuran (1.2 gm, 3.87mmoles), acetic anhydride (0.5 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 1.2 gm (79%) of 2-(p-methoxybenzyl)-3-methyl-4-propyl 5-acetoxybenzofuran, mp. 39°-41° 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-842d9f81f6e444669fa0a774725e8bce
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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