Hydrazine hydrate (1:1) → 2-(Tetrahydrofuran-2-yl)acetohydrazide

HRID 1786181Notes

Reaction equation

HRID 1786181 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][O:7]1)C.O.[NH2:13][NH2:14]>C(O)CCC>[O:7]1[CH2:8][CH2:9][CH2:10][CH:6]1[CH2:5][C:4]([NH:13][NH2:14])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 551345Ethyl Tetrahydrofuran-2-acetate

Product 1

HCID 607781292-(Tetrahydrofuran-2-yl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (rac.)-(tetrahydro-furan-2-yl)-acetic acid ethyl ester (3.84 g, 24 mmol) in n-butanol (24 mL) was treated with hydrazine hydrate (1.4 mL, 29 mmol) and the resulting mixture was then heated under reflux for 3 h. The solvent was evaporated and residual volatile components were azeotropically removed by coevaporation with toluene. Chromatographic purification (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) afforded the title compound as a viscous, colorless oil (1.1 g, 32%). 1H-NMR (300 MHz, DMSO): δ=1.45 (mc, 1H), 1.70-1.95 (m, 3H), 2.13 (dd, J=6 Hz, J=14 Hz, 1H), 2.24 (dd, J=7 Hz, J=14 Hz, 1H), 3.56 (dd, J=8 Hz, J=14 Hz, 1H), 3.72 (dd, J=7 Hz, J=14 Hz, 1H), 4.05 (mc, 1H), 4.16 (s, 2H), 8.94 (s, 1H).

Workup

  1. temperaturethe resulting mixture was then heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was evaporated
  4. customresidual volatile components were azeotropically removed by coevaporation with toluene
  5. customChromatographic purification (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1)

Sources & evidence

ORD record
ord-bbd11b3c07694e559b5256fd8bf9638c
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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