Methyl iodide → 6-[(6-Methoxy-3,7,7-trimethyloct-2-en-1-yl)oxy]-2,3-dihydro-1-benzofuran

HRID 1414831Notes

Reaction equation

[OH:1][CH:2]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:3][CH2:4][C:5]([CH3:18])=[CH:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][O:15][C:11]=2[CH:10]=1.O1CCC[CH2:24]1.[H-].[Na+].CI>CN(C)P(=O)(N(C)C)N(C)C>[CH3:24][O:1][CH:2]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:3][CH2:4][C:5]([CH3:18])=[CH:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][O:15][C:11]=2[CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

0.4 g. of 6-[(6-hydroxy-3,7,7-trimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran are dissolved in 10 ml. of absolute tetrahydrofuran and, while stirring, warmed to 40° C. for 2 hours with 0.5 g. of a 55% by weight sodium hydride suspension in oil. Then 2 ml. of hexamethylphosphoric acid triamide and 1 ml. of methyl iodide are added and the mixture is stirred for 12 hours at room temperature. For the working up, the mixture is poured onto ice-water and extracted twice with diethyl ether. The ether extracts are washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/diethyl ether (19:1 parts by volume) there is obtained 6-[(6-methoxy-3,7,7-trimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran; nD25 = 1.5170.

Workup

additionFor the working up, the mixture is poured onto ice-water
extractionextracted twice with diethyl ether
washThe ether extracts are washed with water and saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-274842afeed347d5824f8787e5d4a7f4
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04002647

Reaction notes

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