Diisopropylamine → 5-Cyano-2-furaldehyde

HRID 1654129

Reaction equation

HRID 1654129 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[O:13]1C=CC=[C:14]1[C:18]#[N:19].P([O-])(O)(O)=[O:21].[K+]>CCCCCC.O1CCCC1>[CH:8]([C:9]1[O:13][C:14]([C:18]#[N:19])=[CH:11][CH:10]=1)=[O:21]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 692452-FuronitrileHCID 516951Monobasic potassium phosphateHCID 178418339Butyllithium

Product 1

HCID 6421395-Cyano-2-furaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

75 ml of tetrahydrofuran and 22.6 ml of diisopropylamine were cooled to -60° C. and 100 ml of 1.6M n-butyllithium in hexane were added over 25 minutes. The mixture was stirred for 1 hour and 13.02 g of 2-furancarbonitrile in 50 ml of tetrahydrofuran were added. The mixture was stirred for 40 minutes at -70° C. and 13 ml of N-dimethylformamide in 25 ml of tetrahydrofuran were added. The mixture was stirred for 2 hours at -70° C. and then poured into an aqueous potassium dihydrogen phosphate solution and extracted with isopropyl ether. The extract was dried and the solvent was evaporated to obtain after chromatography on silica (eluent: 7/3 hexane/ethyl acetate) 3.51 g of the expected product.

Workup

  1. stirringThe mixture was stirred for 40 minutes at -70° C.
  2. stirringThe mixture was stirred for 2 hours at -70° C.
  3. extractionextracted with isopropyl ether
  4. customThe extract was dried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cd0f69afc8744f378e538c4e26adb6bc
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Linked notes

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