Water → Tert-butyl 2-(4-hydroxyphenyl)ethyl hydrazine-1,2-dicarboxylate

HRID 1892486Notes

Reaction equation

HRID 1892486 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[NH:24][NH2:25].O>O1CCCC1.C(OCC)(=O)C>[NH:24]([C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[NH:25][C:1]([O:22][CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=1)=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10393TyrosolHCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazate

Product 1

HCID 58112153Tert-butyl 2-(4-hydroxyphenyl)ethyl hydrazine-1,2-dicarboxylateYield 20.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1,1′-carbonyldiimidazole (1.620 g, 9.989 mmol) in anhydrous tetrahydrofuran (20 ml) was added 2-(4-hydroxyphenyl)ethanol (1.383 g, 10.01 mmol), and the mixture was stirred at room temperature for 3 hr. tert-Butyl carbazate (1.323 g, 10.01 mmol) was added, and the mixture was stirred at room temperature for 1.5 hr. Water (100 ml) and ethyl acetate (100 ml) were added to the reaction mixture, and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 40 g, ethyl acetate:hexane=4:6→5:5). The fractions containing the object product were concentrated under reduced pressure, and the obtained solid was suspended in diisopropyl ether (50 ml) and filtered. The filtered product was washed 3 times with diisopropyl ether and dried under reduced pressure to give tert-butyl 2-(4-hydroxyphenyl)ethyl hydrazine-1,2-dicarboxylate (616.7 mg, 2.08 mmol, yield 20.8%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hr
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 40 g, ethyl acetate:hexane=4:6→5:5)
  9. additionThe fractions containing the object product
  10. concentrationwere concentrated under reduced pressure
  11. filtrationfiltered
  12. washThe filtered product was washed 3 times with diisopropyl ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-d1303a1642f8424bba48a15f0d0044d6
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…