Dimethyl(methylene)ammounium iodide → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuran

HRID 1607257Notes

Reaction equation

HRID 1607257 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]([CH2:18][CH2:19][CH3:20])=[C:14]([OH:21])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[CH3:24][N+:25]([CH3:27])=[CH2:26].[I-]>C(Cl)Cl>[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]([CH2:24][N:25]([CH3:27])[CH3:26])=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[C:14]([OH:21])[C:11]=3[C:12]=2[CH3:13])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

Product 1

HCID 145708982-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuranYield 124.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran (155 mg gm; 0.5mmole) in methylene chloride (2 mL) was reacted with Eschenmoser's salt (dimethyl methylene-ammonium iodide) (105 mg; 0.5mmole) overnight at room temperature. The reaction mixture was concentrated in vacuo. The residue was taken up in ethylacetate, potassium carbonate was added and the mixture was stirred for a period of 15 minutes. The solids were separated and the ethylacetate solution was evaporated to yield 228 mg of 2-(p-methoxybenzyl)--3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuran.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionpotassium carbonate was added
  3. customThe solids were separated
  4. customthe ethylacetate solution was evaporated

Sources & evidence

ORD record
ord-e1af033935b4416ca33f23452964d92d
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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