1,2-Dichloroethane → HCID 69139366, compound

HRID 2221425Notes

Reaction equation

HRID 2221425 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C@H:8]([OH:21])[CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[C:4]([OH:24])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCCl.[C:35](OC(=O)C)(=[O:37])[CH3:36]>O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C@H:8]([OH:21])[CH2:9][N:10]2[C:11](=[O:20])[C:12]3=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]3[C:14]2=[O:15])=[C:4]([O:24][C:35](=[O:37])[CH3:36])[CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 69141906HCID 69141906, compound

Product 1

HCID 69139366HCID 69139366, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a reaction vessel were added (R)-1-(4-chloro-2-hydroxyphenoxy)-3-phthalimido-2-propanol 348 mg (1.00 mmol), sodium carbonate 159 mg (1.50 mmol) and 1,2-dichloroethane 4 mL. After to the mixture was dropped acetic anhydride 122 mg (1.20 mmol), the mixture was stirred at room temperature for 15 hours. After terminating the reaction by adding water, the water layer was removed and the organic layer was washed with an aqueous 5% HCl solution and an aqueous 5% NaCl solution successively. The organic layer was taken and the solvent was evaporated to give crude (R)-1-(4-chloro-2-acetoxyphenoxy)-3-phthalimido-2-propanol 372 mg (yield 92%, chemical purity 97%) as a pale yellow solid.

Workup

  1. customAfter terminating
  2. customthe reaction
  3. customthe water layer was removed
  4. washthe organic layer was washed with an aqueous 5% HCl solution
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a8820295a53549648356a4c3425cabd7
Source dataset
uspto-grants-2008_05
Patent number
US07368608B2

Reaction notes

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