Ethyl Acetate → HCID 57994322, compound

HRID 1009982Notes

Reaction equation

HRID 1009982 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C(OCC)(=O)C>C1COCC1.O.[Cl-].[Na+].O>[CH2:16]([O:15][C:13](=[O:14])[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 974724-Hydroxybenzylamine

Product 1

HCID 57994322HCID 57994322, compoundYield 117.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-hydroxybenzylamine (1 g, 8.1 mmol) in THF (20 ml) and water (20 ml) was cooled down to 0° C. with sodium hydroxide (357 mg, 8.9 mmol). Benzyl chloroformate (1.27 ml, 8.9 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 1 h and at r.t. for 18 hours. Brine (20 ml) and ethyl acetate (20 mL) were added and the phases were separated. The aqueous phase was extracted with EtOAc (20 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness to yield a light pink solid (2.45 g, 100%). 1H NMR (300 MHz, CDCl3), δ: 4.30 (2 H, d, J=5.8 Hz, CH2NH), 5.15 (2 H, s, OCH2), 6.67 (1 H, br. s, NH), 6.78 (2 H, d, J=8.5 Hz, Ar), 7.12 (2 H, d, J=8.1 Hz, Ar), 7.29-7.44 (5 H, m, Ar)

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (20 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4fff76e60179455cb8c59ea43e39538f
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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