Methyl iodide → HCID 71062681, compound

HRID 1506787Notes

Reaction equation

HRID 1506787 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:7][CH2:6]2.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])([CH3:22])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10084055HCID 10084055, compound

Product 1

HCID 71062681HCID 71062681, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1C (30 g, 114 mmol) in DMF (100 mL) was added over a period of 30 min to an ice cold solution of NaH (11.44 g, 286 mmol) in DMF (100 mL), and the mixture was stirred for 10 min. Methyl iodide (21.36 mL, 343 mmol) was then added, and the mixture was stirred for 6 h at room temperature. The reaction was then brought to 0° C., excess NaH was quenched with ice water, and the aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layers were dried over sodium sulfate and filtered, and the filtrate was concentrated under vacuum to give the title compound (30 g, 81%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.96 (d, J=8.4 Hz, 2H), 6.72 (dd, J1=2.4 Hz, J2=8.4 Hz, 1H), 6.62 (s, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.08-2.80 (m, 3H), 2.46 (d, J=15.6 Hz, 1H), 2.39 (dd, J1=4.4 Hz, J2=12.0 Hz, 1H), 1.90 (dt, J1=14 Hz, J2=4.4 Hz, 1H), 1.26 (s, 3H), 1.21 (t, J=7.2 Hz, 1H). ESI-MS m/z: 277 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 6 h at room temperature
  2. customwas then brought to 0° C.
  3. customexcess NaH was quenched with ice water
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×200 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-c618983cd9304727a5efd8f0d292ebf3
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

Loading…