Diisopropylamine → 2-Thiophenecarboxaldehyde, 4,5-dichloro-

HRID 1654131Notes

Reaction equation

HRID 1654131 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.[Cl:13][C:14]1[S:15]C=C[C:18]=1[Cl:19].P([O-])(O)(O)=[O:21].[Na+]>O1CCCC1.CN(C)C=O>[Cl:19][C:18]1[CH:7]=[C:5]([CH:6]=[O:21])[S:15][C:14]=1[Cl:13]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 140207Thiophene, 2,3-dichloro-HCID 23672064Monosodium phosphateHCID 178418339Butyllithium

Product 1

HCID 1494242-Thiophenecarboxaldehyde, 4,5-dichloro-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

11.1 g of diisopropylamine in 100 ml of tetrahydrofuran were cooled to -60° C., 49 ml of n-butyllithium were added over 10 minutes. The mixture was stirred for 30 minutes and 10 g of 2,3-dichlorothiophene were added at -60° C. The mixture was stirred for 45 minutes and then 6 m1 of dimethylformamide and 10 ml of tetrahydrofuran were added. The mixture was stirred for 1 and a half hours, allowed to return to room temperature, poured into a saturated aqueous sodium dihydrogenphosphate solution and extracted with isopropyl ether. The solvent was evaporated and, after chromatography on silica (eluent: 95/5 hexane/ethyl acetate), 10.16 g of the expected product were obtained.

Workup

  1. stirringThe mixture was stirred for 45 minutes
  2. stirringThe mixture was stirred for 1 and a half hours
  3. customto return to room temperature
  4. extractionextracted with isopropyl ether
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2e9d3e95778b41dd87a9ba5027be5b93
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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