Iodoethane → HCID 71062915, compound

HRID 1506792Notes

Reaction equation

HRID 1506792 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+].[CH2:22](I)[CH3:23]>CN(C=O)C>[CH2:22]([C:8]1([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13])[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10084055HCID 10084055, compound

Product 1

HCID 71062915HCID 71062915, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1C (10 g, 38.16 mmol) in DMF (60 mL) was added over a period of 30 min to an ice cold solution of NaH (2.29 g, 95.41 mmol) in DMF (40 mL), and the mixture was stirred for 10 min. Ethyl iodide (17.86 g, 114.48 mmol) was then added, and the mixture was stirred for 2 h at room temperature. The reaction was then brought to 0° C., excess NaH was quenched with ice water and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and filtered, and the filtrate was concentrated under vacuum to give the title compound (7.0 g, 64%) as a solid. 1H NMR (300 MHz, CDCl3): δ 8.03 (d, J=9.0 Hz, 1H), 6.82 (dd, J1=2.4 Hz, J2=8.7 Hz, 1H), 6.6 (d, J=2.1 Hz, 1H), 4.1 (q, J=7.2 Hz, 2H), 3.8 (s, 3H), 3.12-2.9 (m, 3H), 2.47 (d, J=15.9 Hz, 1H), 2.42 (m, 1H), 2.03 (dt, J1=13.5 Hz, J2=4.5 Hz, 1H), 1.8-1.6 (m, 2H), 1.21 (t, J=7.2 Hz, 3H), 0.9 (t, J=7.5 Hz, 3H). ESI-MS m/z=291 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 2 h at room temperature
  2. customwas then brought to 0° C.
  3. customexcess NaH was quenched with ice water
  4. extractionthe mixture was extracted with ethyl acetate (2×100 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-99ea074ce26146f78dd5541a6c028eb6
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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