Acetic Anhydride → HCID 14579782, compound

HRID 1607252Notes

Reaction equation

HRID 1607252 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.[C:25](OC(=O)C)(=[O:27])[CH3:26].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[C:17]([Cl:18])=[CH:16][C:15]([CH2:19][CH2:20][CH3:21])=[C:14]([O:22][C:25](=[O:27])[CH3:26])[C:11]=3[C:12]=2[CH3:13])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 128132L 656224

Product 1

HCID 14579782HCID 14579782, compoundYield 91%

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), 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 100 mg (91%) of 2-(p-methoxy benzyl)-3-methyl-4-acetoxy-5-propyl 7-chlorobenzofuran, mp. 119°-120° 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-200117d2436743f48db6a900805786f9
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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