Methyl iodide → HCID 14234360, compound

HRID 35526Notes

Reaction equation

HRID 35526 reaction equation
[H-].[K+].[CH3:3]CCCCC.[OH:9][CH2:10][CH:11]1[C:20]23[CH2:21][CH2:22][CH:13]([CH:14]4[O:29][C:28]5[C:30]([O:34][CH3:35])=[CH:31][CH:32]=[CH:33][C:27]=5[C:15]42[CH2:16][CH2:17][N:18]([CH2:24][CH2:25][CH3:26])[C:19]3=[O:23])[CH2:12]1.CI>O1CCCC1>[CH3:35][O:34][C:30]1[C:28]2[O:29][CH:14]3[CH:13]4[CH2:22][CH2:21][C:20]5([CH:11]([CH2:10][O:9][CH3:3])[CH2:12]4)[C:15]3([CH2:16][CH2:17][N:18]([CH2:24][CH2:25][CH3:26])[C:19]5=[O:23])[C:27]=2[CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 82127Potassium hydrideHCID 14234358HCID 14234358, compound

Product 1

HCID 14234360HCID 14234360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 9 g of 35% potassium hydride in oil, prewashed with hexane, and 40 mL of tetrahydrofuran was added 4.05 g of 5-hydroxymethyl-9-methoxy-3-n-propyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one. The mixture was stirred at room temperature for 30 minutes, and then heated under reflux for 30 minutes. Methyl iodide (8 mL) was added to the cooled mixture which was then heated under reflux for one hour. Excess hydride was destroyed by addition of 10 mL of methanol, and the solvent was removed. The product was taken up in methylene chloride/water, and the aqueous layer was extracted with methylene chloride. Removal of the solvent gave 4.45 g of 9-methoxy-5-methoxymethyl-3-n-propyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one. NMR spectrum (δ in CDCl3); 6.8 (m, 2H); 6.5 (m, 1H); 4.5 (s, 1H); 3.9 (s, 3H); 3.3 (s, 3H) and 1.0 (t, 3H), among others.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperaturewas then heated
  4. temperatureunder reflux for one hour
  5. customExcess hydride was destroyed by addition of 10 mL of methanol
  6. customthe solvent was removed
  7. extractionthe aqueous layer was extracted with methylene chloride
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-684fcfbdf59941448ffecf555fb8f751
Source dataset
uspto-grants-1988_08
Patent number
US04767764

Reaction notes

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