Dimethylformamide → (R)-2-chloro-2-oxo-1-phenylethyl pivalate

HRID 389401Notes

Reaction equation

HRID 389401 reaction equation
[C:1]([OH:11])(=O)[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].CN(C)C=O.S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[C:12]([O:3][C@H:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:1]([Cl:26])=[O:11])(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11914(-)-Mandelic acidHCID 24386Thionyl ChlorideHCID 62493Pivaloyl chloride

Product 1

HCID 86649875(R)-2-chloro-2-oxo-1-phenylethyl pivalate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

(R)-Mandelic acid (10 g, 65.7 mmol) was dissolved in toluene (20 mL) at which point pivaloyl chloride (10.2 mL, 82.9 mmol) was added. This mixture was stirred at 60° C. for 3 hours. After cooling the reaction mixture to 30° C., toluene (10 mL), N,N-dimethylformamide (0.3 mL) and thionyl chloride (10 mL) were added. The reaction mixture was stirred at 35° C. for 2 hours and then at 50° C. for 4 hours. Then the mixture was evaporated to dryness to furnish 14.5 g (R)-2-chloro-2-oxo-1-phenylethyl pivalate as a yellow oil.

Workup

  1. additionwas added
  2. temperatureAfter cooling the reaction mixture to 30° C.
  3. stirringThe reaction mixture was stirred at 35° C. for 2 hours
  4. waitat 50° C. for 4 hours
  5. customThen the mixture was evaporated to dryness

Sources & evidence

ORD record
ord-f3fd3861945d4d97b0753cd83a03248c
Source dataset
uspto-grants-2013_02
Patent number
US08378143B2

Reaction notes

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