Tetrahydrofuran → (4-Benzyloxy-phenyl)-acetic acid hydrazide

HRID 1927230Notes

Reaction equation

HRID 1927230 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](Cl)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C(N(CC)CC)C.O.[NH2:32][NH2:33]>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:32][NH2:33])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 113574424-Benzyloxyphenylacetyl Chloride

Product 1

HCID 59287387(4-Benzyloxy-phenyl)-acetic acid hydrazide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-benzyloxyphenylacetyl chloride (1.1 g) and THF (10 mL) were added triethylamine (1.8 mL) and hydrazine hydrate (0.20 mL) at room temperature, which was stirred at the same temperature for 7.5 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with saturated brine. The solvent was evaporated under a reduced pressure, after which the residue was purified by silica gel chromatography (methanol:ethyl acetate=1:30) to obtain the titled compound (0.23 g).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. customThe solvent was evaporated under a reduced pressure
  4. customafter which the residue was purified by silica gel chromatography (methanol:ethyl acetate=1:30)

Sources & evidence

ORD record
ord-7b8bdd7125be462fb8d8e4b34ad552ff
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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