Tetrahydrofuran → HCID 178447090, compound

HRID 2231159Notes

Reaction equation

HRID 2231159 reaction equation
[H-].[Li+:2].[C:3]([C:5]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:6]([OH:17])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])#[N:4].C1COCC1>CCOCC>[Li+:2].[C:3]([C:5]([C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22])=[C:6]([O-:17])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])#[N:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 62714Lithium hydrideHCID 183149Pentanenitrile, 2-[(4-chloro-2-nitrophenyl)hydroxymethylene]-4,4-dimethyl-3-oxo-

Product 1

HCID 178447090HCID 178447090, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred slurry of 0.36 g of LiH in 15 ml of dry ether under N2 at room temperature was rapidly added a solution of 1.5 g of 2-cyano-4,4-dimethyl-1-hydroxy-3-oxo-1-(2-nitro-4-chlorophenyl)-1-pentene dissolved in 15 ml of dry ether. The reaction mixture turned brown and a precipitate formed with 5 min. Enough dry THF was added to dissolve the solid and the mixture allowed to stir overnight at ambient temperature. The reaction was filtered and the filtrate concentrated under reduced pressure to yield 1.25 g of product as a yellow solid, m.p. >230° C. (decomp.).

Workup

  1. customa precipitate formed with 5 min
  2. dissolutionto dissolve the solid
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-c14e22718d8e41829161a516e075a01e
Source dataset
uspto-grants-1988_11
Patent number
US04781750

Reaction notes

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