Hydrochloric Acid → HCID 53400572, compound

HRID 886593Notes

Reaction equation

HRID 886593 reaction equation
C([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)[OH:6])C.[H-].[Na+].[CH3:17]I.[Cl-].[Na+].Cl>C1COCC1>[Br:13][C:9]1[CH:8]=[C:7]([CH:5]([O:6][CH3:17])[C:4]([OH:3])=[O:14])[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12252958HCID 12252958, compound

Product 1

HCID 53400572HCID 53400572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-Bromomandelic acid ethyl ester (0.5 g, 2.2 mmol) in THF (5 mL) at 0° C. was added sodium hydride (352 mg, 60% in mineral oil, 8.8 mmol) and the resulting mixture was stirred at 0° C. for 15 minutes. Methyl iodide (1.9 g, 13.2 mmol) was added and the resulting mixture was stirred at 0° C. for 10 minutes and warmed to room temperature for 15 minutes. Saturated sodium chloride (10 mL) was added and 1 N hydrochloric acid was added to adjust the pH to 4. The resulting mixture was extracted with ethyl acetate (5 mL×4) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue (0.43 g, 80%) was used in next step without further purification. MS: m/z 245 (M+H+).

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for 10 minutes
  2. temperaturewarmed to room temperature for 15 minutes
  3. extractionThe resulting mixture was extracted with ethyl acetate (5 mL×4)
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue (0.43 g, 80%) was used in next step without further purification

Sources & evidence

ORD record
ord-3358a95ee346464097ec2323b3ed9ffc
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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