Methyl iodide → HCID 12723453, compound

Reaction equation

[H-].[Na+].[CH:3]1([OH:10])[CH2:8][CH2:7]C(O)C=C1.[CH3:11]I.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH3:15][O:16][CH:17]1[CH2:13][CH2:14][CH:3]([O:10][CH3:11])[CH:8]=[CH:7]1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 5508252-Cyclohexene-1,4-diol

Product 1

HCID 12723453HCID 12723453, compoundYield 91%

Procedure

Lit., J. Org. Chem., 53:5695 (1988). To 14.3 g (328 mmol) sodium hydride (55% dispersion in oil) was added dropwise at 0° C. with stirring a solution of 10.1 g (88.5 mmol) (1RS,4RS)-cyclohex-2-ene-1,4-diol in 100 ml THF. 34 ml (546 mmol) methyl iodide was then added and stirring continued for an additional 48 h at room temperature. The reaction was quenched with saturated ammonium chloride solution and extracted with ether. The combined organic extracts were washed successively with saturated ammonium chloride solution and saturated brine, dried over sodium sulphate, and concentrated in vacuo to afford 11.5 g (91%) of the title compound as a yellow oil. 1H NMR d (250 MHz, CDCl3) 5.90 (2H, s), 3.82 (2H, br t), 3.37 (6H, s), 2.10 (2H, m), 1.51 (2H, m).