Tetrahydrofuran → HCID 86673387, compound

HRID 1023357Notes

Reaction equation

HRID 1023357 reaction equation
C1COCC1.[H-].[Na+].[CH3:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:27])[C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1)[CH:12]=O.[CH3:28][CH2:29][O:30][C:31]([CH3:33])=[O:32]>O>[CH3:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:33]/[C:31]([O:30][CH2:29][CH3:28])=[O:32])[CH:14]=[C:15]([CH3:27])[C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86673388HCID 86673388, compound

Product 1

HCID 86673387HCID 86673387, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF (100 mL) solution of triethyl phosphonoacetate (44.0 mL) was slowly added NaH (60% dispersion in mineral oil, 8.8 g) at 0° C. After stirring for 1 hour, a THF (200 mL) solution of 3,5-dimethyl-4-[(5-nitropyridin-2-yl)oxy]benzaldehyde (54.5 g) was added to the reaction mixture. After stirring at room temperature for 2 hours, AcOEt and H2O were added to the reaction mixture. The resulting precipitate was collected to give ethyl (E)-3-{3,5-dimethyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate as a white powder (40.9 g).

Workup

  1. customat 0° C
  2. stirringAfter stirring at room temperature for 2 hours
  3. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-b4426196479f4aea8e2ce12628c4f350
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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