N,N,N',N'-Tetramethylmethanediamine → 5-((Dimethylamino)methyl)-2-furanmethanol

HRID 67877

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].[CH3:8][N:9]([CH2:11]N(C)C)[CH3:10]>>[CH3:8][N:9]([CH2:11][C:5]1[O:1][C:2]([CH2:6][OH:7])=[CH:3][CH:4]=1)[CH3:10]

Participants

Reactant 2

HCID 5829N,N,N',N'-Tetramethylmethanediamine

HCID 7361Furfuryl Alcohol

Product 1

HCID 849065-((Dimethylamino)methyl)-2-furanmethanol

Procedure

In a series of experiments with 2-furanmethanol we have found that the use of bis(dimethylamino)methane gives better yields of 5-(dimethylaminomethyl)-2-furanmethanol than those obtained using dimethylamine and a source of formaldehyde (e.g. aqueous formaldehyde, paraformaldehyde and trioxan). Furthermore the product obtained after distillation was also purer. The yields referred to above were 76-94% and these compare very favourably with the yields reported by R. F. Holdren (12%) (J. Amer. Chem. Soc. 69(464)1947) and Gill and Ing (70%) (J. Chem. Soc. 4728 (1958)).

Workup

customgives better

Sources & evidence

ORD record: ord-47a1553ef51b4b7ba252c6f4694c51f6
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04347191

Linked notes

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