Sodium hydride → HCID 71062618, compound

HRID 1506783Notes

Reaction equation

HRID 1506783 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+].[F:22][C:23]([F:27])([F:26])[CH2:24]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])([CH2:24][C:23]([F:27])([F:26])[F:22])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 10084055HCID 10084055, compound

Product 1

HCID 71062618HCID 71062618, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1C (25 g, 95 mmol) in DMF (40 mL) was added over a period of 30 min to an ice cold solution of NaH (9.53 g, 238 mmol) in DMF (20 mL), and the mixture was stirred for 10 min. Trifluoroethyl iodide (50 g, 238 mmol) was then added, and the mixture was stirred for 3 h at room temperature. The reaction mixture was then brought to 0° C., excess NaH was quenched with ice water, and the aqueous layer with 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 (16.2 g, 42%) as a solid. 1H NMR (300 MHz, CDCl3): δ 8.02 (d, J=9.3 Hz, 1H), 6.85 (dd, J1=2.7 Hz, J2=9.0 Hz, 1H), 6.68 (d, J=2.7 Hz, 1H), 4.1 (q, J=6.9 Hz, 2H), 3.86 (s, 3H), 3.05-2.9 (m, 4H), 2.6-2.4 (m, 4H), 1.23 (t, J=6.9 Hz, 3H). ESI-MS m/z: 345 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 3 h at room temperature
  2. customwas then brought to 0° C.
  3. customexcess NaH was quenched with ice water
  4. extractionthe aqueous layer with 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-2010683be3784206ae84505780ec6949
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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