Sodium Iodide → 7-Methoxy-2-(5-methoxyhept-1-y)bicyclo[3.3.0]octane

HRID 1722385Notes

Reaction equation

HRID 1722385 reaction equation
[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[C:9]1(O)[CH2:10][CH2:11][CH2:12]2.[CH3:19][O:20]C(CC)CCCCC1CCC2C1CC(O)C2.[I-].[Na+].CI>O1CCCC1>[CH3:19][O:20][CH:11]1[CH2:10][CH:9]2[CH:13]([CH2:14][CH2:15][CH:8]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:17][CH3:18])[CH2:12]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6328Methyl iodideHCID 15053012Octahydro-4-(5-methoxyheptyl)-2-pentalenolHCID 200287172-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octanol

Product 1

HCID 150530477-Methoxy-2-(5-methoxyhept-1-y)bicyclo[3.3.0]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The starting material, 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octanol {octahydro-4-(5-methoxyheptyl)-2-pentalenol} (1.0 g, 3.9 mmoles) is added to a reaction vessel containing sodium iodide (0.12 g, 4.9 mmoles) and tetrahydrofuran (12 ml). The solution is stirred while methyl iodide (0.84 g, 5.9 mmoles) is rapidly added. The reaction is heated in a 50° C. water bath for 4 hours. The water bath is removed and the reaction neutralized with the addition of water (5 ml). The organic phase is separated and the aqueous phase extracted with ether (2×50 ml). The ether extracts are combined and washed with brine (50 ml). The solution is dried over anhydrous magnesium sulfate and the solvent removed under vacuum leaving a clear yellow oil. The product is then kugelrohred under reduced pressure leaving a pale yellow oil (0.8 g, 3.1 mmoles).

Workup

  1. additionis added to a reaction vessel
  2. additionis rapidly added
  3. customThe water bath is removed
  4. additionthe reaction neutralized with the addition of water (5 ml)
  5. customThe organic phase is separated
  6. extractionthe aqueous phase extracted with ether (2×50 ml)
  7. washwashed with brine (50 ml)
  8. dry with materialThe solution is dried over anhydrous magnesium sulfate
  9. customthe solvent removed under vacuum
  10. customleaving a clear yellow oil

Sources & evidence

ORD record
ord-2f68bce189284e71b6a32b3dcfcc9d01
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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