Tetrahydrofuran → HCID 86711818, compound

HRID 623730Notes

Reaction equation

HRID 623730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[N+]([O-])=O)\[CH3:10])=[C:4]([F:14])[CH:3]=1.[N+:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[C-:16].C1COCC1>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:10])=[CH:16][NH:15][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 533707Ethyl isocyanoacetateHCID 86711817HCID 86711817, compound

Product 1

HCID 86711818HCID 86711818, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of (E)-4-chloro-2-fluoro-1-(2-nitroprop-1-enyl)benzene (5 g, 23.2 mmol) and ethyl 2-isocyanoacetate (2.65 mL, 24.4 mmol) in a mixture of dry THF (20 mL) and i-PrOH (20 mL) was added 2.6 mmol TBD/g polymer (9.8 g, 25.5 mmol). The suspension was stirred at room temperature for 5 d. The reaction mixture was filtered off and the residue was washed with i-PrOH/THF (1:1, 30 mL). The filtrate was concentrated to give the desired product (5.7 g, 87%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered off
  2. washthe residue was washed with i-PrOH/THF (1:1, 30 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-66fb0c1ed19f453eb7a4b6bf1e2c5ed2
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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