Ethylene carbonate → 2-(1,3-Benzoxazol-4-yloxy)ethanol

HRID 1789725Notes

Reaction equation

HRID 1789725 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[C:13]2[N:14]=[CH:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1.C1(=O)O[CH2:20][CH2:19][O:18]1>CN(C=O)C.O.CO>[O:16]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([O:7][CH2:20][CH2:19][OH:18])[C:13]=2[N:14]=[CH:15]1

Participants

7

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 137206971,3-Benzoxazol-4-ol

Product 1

HCID 220363922-(1,3-Benzoxazol-4-yloxy)ethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

K2CO3 (254 mg, 1.84 mmol) was added to a stirred solution of 4-hydroxybenzoxazole* (248 mg, 1.84 mmol) in DMF (5 mL) at room temperature. The mixture was heated at 90° C. for 15 min and ethylene carbonate (176 mg, 2.00 mmol) was added. The mixture was stirred at 150° C. for 2 h and allowed to attain room temperature. The mixture was diluted with water (2 mL) and MeOH (2 mL), and concentrated. The residue was partitioned between water and CH2Cl2. The aqueous layer was separated and extracted with CH2Cl2 (2×10 mL). The organic phases were pooled and washed with water and brine, and dried over MgSO4. The filtrate was concentrated to give the product as a brown oil that slowly solidified: yield 278 mg (84%); mp 47-49° C. Anal. (C9H9NO3) C, H, N.

Workup

  1. customto attain room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between water and CH2Cl2
  4. customThe aqueous layer was separated
  5. extractionextracted with CH2Cl2 (2×10 mL)
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1ac4601af65d4780834d083041de219d
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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