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

HRID 127305Notes

Reaction equation

HRID 127305 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, 62.52; 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-715b70e611eb499ebeb54da2ac9c74f6
Source dataset
uspto-grants-1981_03
Patent number
US04255440

Reaction notes

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