Methyl iodide → HCID 58934897, compound

HRID 855157Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

To a chilled solution (−78° C.) of 9.33 g (47.55 mmol) of 2-(3-fluorophenoxy)-tetrahydro-2H-pyran in 150 mL of THF was added 38 mL (95.1 mmols) of n-BuLi (2.5 M soln in hexanes). The reaction mixture was stirred at −78° C. for 45 minutes and slowly added 11.9 mL (190.2 mmol) of methyl iodide via syringe. The reaction was allowed to warm to room temperature and was stirred overnight. Quenched reaction with satd ammonium chloride and transferred to a round bottom flask. Removed volatiles in vacuo and partitioned mixture between EtOAc and water. Separated layers and washed organics with water (×2) and brine. Dried over Na2SO4, filtered, and concd to afford a 9.01 g (90%) of a yellow oil: 1H NMR (CDCl3/400 MHz) 1.46-2.09 (m, 6H), 2.21 (d, 3H, J=2.0 Hz), 3.60-3.65 (m, 1H), 3.86-3.92 (m, 1H), 5.44 (t, 1H, J=3.2 Hz), 6.70 (t, 1H, J=8.8 Hz), 6.90 (d, 1H, J=8.4 Hz), 7.08 (dd, 1H, J=8.0, 15.2 Hz); HRMS (EI+) m/z calcd for (C12H15FO2) 210.1056, found 210.1070.

Workup

temperatureto warm to room temperature
stirringwas stirred overnight
customQuenched
customreaction with satd ammonium chloride
customtransferred to a round bottom flask
customRemoved volatiles in vacuo and partitioned mixture between EtOAc and water
washSeparated layers and washed organics with water (×2) and brine
dry with materialDried over Na2SO4
filtrationfiltered

Sources & evidence

ORD record: ord-0ceb9fef0726404d805ac0dead4c287a
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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