Formaldehyde → 5-(Dimethylaminomethyl)-4-methyl-2-furanmethanol

HRID 1577503Notes

Reaction equation

HRID 1577503 reaction equation
[CH3:1][N:2]([CH3:10])[CH2:3][C:4]1[O:5][CH:6]=[CH:7][C:8]=1[CH3:9].C([Li])CCC.[CH2:16]=[O:17].O>O1CCCC1.CCCCCC>[CH3:1][N:2]([CH2:3][C:4]1[O:5][C:6]([CH2:16][OH:17])=[CH:7][C:8]=1[CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 100347492-Dimethylaminomethyl-3-methylfuranHCID 178418339Butyllithium

Product 1

HCID 205709095-(Dimethylaminomethyl)-4-methyl-2-furanmethanolYield 63.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of N,N,3-trimethyl-2-furanmethanamine (10.3 g) in dry tetrahydrofuran (200 ml) under nitrogen was treated over 2 hr with 1.6 M n-butyl lithium in hexane 846.2 ml) at -40° to -45° C. After stirring for 2 hr at room temperature paraformaldehyde (2.3 g) in dry tetrahydrofuran (100 ml) was added and the solution stirred overnight. Water (10 ml) was added and the solvent evaporated. Ethyl acetate (200 ml) and sodium sulphate were added and the organic phase was evaporated giving an oily residue which was distilled (85°/0.1 mm) affording the title compound (8 g).

Workup

  1. additionwas added
  2. customthe solvent evaporated
  3. additionEthyl acetate (200 ml) and sodium sulphate were added
  4. customthe organic phase was evaporated
  5. customgiving an oily residue which
  6. distillationwas distilled (85°/0.1 mm)

Sources & evidence

ORD record
ord-52f9c2e5704e4df9816d527246f83d59
Source dataset
uspto-grants-1981_09
Patent number
US04288443

Reaction notes

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