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

HRID 1789562Notes

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[CH:9]1[CH2:10][CH:11]([OH:16])[CH2:12]2.[I-].[Na+].[CH3:21]I>O1CCCC1>[CH3:21][O:16][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

Conditions

Temperature: 50 °C

Procedure

The starting material, 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]7 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

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

Sources & evidence

ORD record: ord-84333a5b19d34faba23cff08212dd607
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689345

Reaction notes

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