Acetic Anhydride → [5-[4-(Dimethylamino)butyl]-2-furanyl]methyl ethanoate

HRID 426471Notes

Reaction equation

HRID 426471 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[O:11][C:10]([CH2:12][OH:13])=[CH:9][CH:8]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].C([O-])(=O)C.[Na+]>C1C=CC=CC=1.O>[C:15]([O:13][CH2:12][C:10]1[O:11][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:14])=[CH:8][CH:9]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 23452131HCID 23452131, compound

Product 1

HCID 23452115[5-[4-(Dimethylamino)butyl]-2-furanyl]methyl ethanoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 5-[4-(dimethylamino)butyl]-2-furanmethanol (4.9 g), acetic anhydride (25 g) and fused and powdered sodium acetate (10 g) in benzene (25 ml) was stirred at room temperature for 24 hr. The reaction was diluted with water (100 ml) and extracted with ethyl acetate. The combined extracts were distilled to afford a clear colourless oil b.p. 100°, 0.5 mm Hg. Found: C, 65.62; H, 9.03; N, 5.95. Calc. for C13H21NO3 : C, 65.24; H, 8.85; N, 5.85%.

Workup

  1. extractionextracted with ethyl acetate
  2. distillationThe combined extracts were distilled

Sources & evidence

ORD record
ord-884c654d1a2147a9b44eeb5cf22eac93
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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