Water → HCID 20570918, compound

HRID 1577501Notes

Reaction equation

HRID 1577501 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([C:5]1[O:6][CH:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][N:2]([CH3:13])[CH2:3][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 20570904HCID 20570904, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20570918HCID 20570918, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dimethyl-3-(1-methylethyl)-2-furanecarboxamide (12 g) in dry tetrahydrofuran (250 ml) was treated with lithium aluminium hydride (4.2 g). After 1 hour water (6 ml) was added and the filtered solution evaporated in vacuo. The residue was dissolved in 1 M hydrochloric acid (100 ml) and the solution was washed with diethyl ether (100 ml). The aqueous phase was basified and extracted with diethyl ether (2×150 ml), which was dried over anhydrous sodium sulphate. The solvent was removed in vacuo to yield the title compound (7 g) as an oil.

Workup

  1. customthe filtered solution evaporated in vacuo
  2. dissolutionThe residue was dissolved in 1 M hydrochloric acid (100 ml)
  3. washthe solution was washed with diethyl ether (100 ml)
  4. extractionextracted with diethyl ether (2×150 ml), which
  5. dry with materialwas dried over anhydrous sodium sulphate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6b820ed1807f445c9f19370f85f509f3
Source dataset
uspto-grants-1981_09
Patent number
US04288443

Reaction notes

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