Ethyl Acetate → 3-[(2-Methoxyethoxy)carbonylamino]benzyl alcohol

HRID 639719Notes

Reaction equation

HRID 639719 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Cl[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[O:12].C(OCC)(=O)C>O1CCCC1>[CH3:17][O:16][CH2:15][CH2:14][O:13][C:11]([NH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6])=[O:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 694002-Methoxyethyl chloroformate2×HCID 802933-Aminobenzyl alcohol

Product 1

HCID 673477703-[(2-Methoxyethoxy)carbonylamino]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 15.0 g of 3-aminobenzyl alcohol in 120 ml of tetrahydrofuran was added dropwise a solution of 18 ml of 2-methoxyethyl chloroformate in 70 ml of tetrahydrofuran under ice-cooling. After stirred for 30 minutes under ice-cooling and then at room temperature for 30 minutes, additional 2 ml of 2-methoxyethyl chloroformate was added, and the mixture was stirred at room temperature for 1 hour. After ethyl acetate was added, the mixture was washed successively with an aqueous saturated sodium bicarbonate solution and then an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated to obtain 30.2 g of 3-[(2-methoxyethoxy)carbonylamino]benzyl alcohol.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitat room temperature for 30 minutes
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. washthe mixture was washed successively with an aqueous saturated sodium bicarbonate solution
  6. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fade4e6a07bf4952974b2573a70727ec
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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