Water → HCID 131724401, compound

HRID 2084696Notes

Reaction equation

HRID 2084696 reaction equation
[C:1]([C:3]1[C:4](=[C:11]([C:14]#[N:15])[C:12]#[N:13])[O:5][C:6]([CH3:10])([CH3:9])[C:7]=1[CH3:8])#[N:2].[C:16]([SiH2:20][O:21][C:22]([CH3:49])([CH3:48])[CH:23]1[CH2:28][O:27][C:26]2=[C:29]([CH:34]=[CH:35][C:36]3[CH:41]=[CH:40][C:39]([N:42]([CH2:46][CH3:47])[CH2:43][CH2:44][OH:45])=[CH:38][CH:37]=3)[S:30][C:31]([CH:32]=O)=[C:25]2[O:24]1)([CH3:19])([CH3:18])[CH3:17].O>N1CCCCC1.C(Cl)(Cl)Cl>[C:16]([SiH2:20][O:21][C:22]([CH3:48])([CH3:49])[CH:23]1[CH2:28][O:27][C:26]2=[C:29]([CH:34]=[CH:35][C:36]3[CH:37]=[CH:38][C:39]([N:42]([CH2:46][CH3:47])[CH2:43][CH2:44][OH:45])=[CH:40][CH:41]=3)[S:30][C:31]([CH:32]=[CH:8][C:7]3[C:6]([CH3:9])([CH3:10])[O:5][C:4](=[C:11]([C:12]#[N:13])[C:14]#[N:15])[C:3]=3[C:1]#[N:2])=[C:25]2[O:24]1)([CH3:17])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 99903452-[3-Cyano-4,5,5-trimethylfuran-2(5H)-ylidene]malononitrileHCID 131724402HCID 131724402, compound

Product 1

HCID 131724401HCID 131724401, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6212ChloroformSolvent2×

Procedure

15 mL of anyhdrous chloroform was added to 1.99 g (0.010 mol) of 2-(3-cyano-4,5,5-trimethyl-5H-furan-2-ylidene)-malononitrile, and 2.91 g of 4 (0.007 mol). Once in solution, 5 drops of piperidine were added and the reaction mixture was stirred at reflux. The reaction went to completion in 2 h. The crude reaction mixture was poured into water, and an equal amount of chloroform was added. The organic layered was washed three times with water, dried over MgSO4, and filtered. The solvent was removed under reduced pressure. The compound was purified on a silica column with a hexane/ethyl acetate mobile phase to yield 1.5 g of 5 (37.5% yield).

Workup

  1. temperatureat reflux
  2. customThe crude reaction mixture
  3. washThe organic layered was washed three times with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe compound was purified on a silica column with a hexane/ethyl acetate mobile phase

Sources & evidence

ORD record
ord-237c56c0a4d64851ae61493574648391
Source dataset
uspto-grants-2004_04
Patent number
US06716995B2

Reaction notes

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