Methyl iodide → HCID 22026351, compound

HRID 1793228Notes

Reaction equation

[CH3:1][C:2]1[C:3](=[O:14])[C:4]([CH3:13])([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:5][CH2:6][CH:7]=1.[Li+].[CH3:16]C([N-]C(C)C)C.CI>C1COCC1.CC(OC)(C)C>[CH3:1][C:2]1([CH3:16])[CH:7]=[CH:6][CH2:5][C:4]([CH3:13])([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[C:3]1=[O:14]

Participants

Conditions

Temperature: -78 °C

Procedure

2,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone (5.00 g, 26 mmol) was added to a solution of LDA (prepared from diisopropylamine (3.15 g, 31.2 mmol) and n-BuLi (1.6M in hexane, 19.5 ml, 31.2 mmol)) in THF (50 ml) at −78° C. The mixture was stirred for 1 h at −78° C. Methyl iodide (5.54 g, 39 mmol) was added and the solution was allowed to warm to room temperature over night. The mixture was diluted with MTBE and washed with portions of H2O and brine, dried (MgSO4) and concentrated in vacuo to yield 7 g of a slightly yellow oil which was distilled (bp.42° C./0.005 mbar) to give 4.5 g (84%) of an olfactorily clean oil. 1H-NMR (400 MHz, CDCl3): 5.72-5.68 (m, 1H), 5.63-5.59 (m, 1H), 5.06-4.99 (m, 1H), 2.36-2.08 (m, 4H), 1.70 (s, 3H), 1.59 (s, 3H), 1.15 (s, 3H), 1.12 (s, 3H), 1.07 (s, 3H) ppm. GC/MS (EI): 206 (M+, 15), 191 (8), 137 (19), 123 (25), 109 (100), 96 (34), 91 (9), 81 (28), 67 (24), 41 (33). IR (ATR): 3023s, 2966s, 2926m, 1703vs, 1456s, 1376m, 1203w, 1033s, 713s cm−1.

Workup

temperatureto warm to room temperature over night
washwashed with portions of H2O and brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto yield 7 g of a slightly yellow oil which
distillationwas distilled (bp.42° C./0.005 mbar)
customto give 4.5 g (84%) of an olfactorily clean oil

Sources & evidence

ORD record: ord-f9f153e8525b4067966b861eb0782cb3
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078570B2

Reaction notes

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