Dimethylformamide → Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate

HRID 433935Notes

Reaction equation

HRID 433935 reaction equation
[OH:1][C@@H:2]([C:6]([O:19][CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C[O-].[Na+].[CH3:24]N(C=O)C.COS(OC)(=O)=O>O>[OH:1][C@@H:2]([C:6]([O:19][CH3:20])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH3:24])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 15380898(2S)-2-Hydroxy-3-methoxy-3,3-diphenylpropanoic acid

Product 1

HCID 10636938Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

54.4 g (200 mmol) of (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid were introduced with 10.8 g (200 mmol) of sodium methoxide into 300 ml of DMF. 21 ml (210 mmol) of dimethylsulfate were added dropwise to this suspension over 15 minutes, during which the temperature rises to 50° C. and the suspension becomes mobile. The mixture was stirred overnight and then added to 1.5 l of water and ice. The aqueous phase was extracted twice with 500 ml of ether, and the ether phase was in turn washed with 200 ml of water twice. The organic phase was dried over magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off. 55.8 g of an oil were isolated and were immediately processed further.

Workup

  1. customrises to 50° C.
  2. extractionThe aqueous phase was extracted twice with 500 ml of ether
  3. washwashed with 200 ml of water twice
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-92f79e17777b490fa5f4ccb530e86fb3
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

Loading…