Water → HCID 18936595, compound

HRID 1939832Notes

Reaction equation

HRID 1939832 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13](CI)[O:12][C:11](=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17]([O-:20])([O-])=[O:18].[Cs+].[Cs+].[CH3:23]COCC.O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:10]2[CH2:11][O:12]2)[CH2:13][C:17]([O:20][CH3:23])=[O:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 18936612HCID 18936612, compound

Product 1

HCID 18936595HCID 18936595, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a solution of the product of step 1 (1.5 g, 4.02 mmol) in dry CH3OH (15 mL) under N2 with Cs2CO3 (1.57 g, 4.8 mmol, 1.2 eq). Stir for 30 min, then pour the suspension into Et2O (200 mL)/water (100 mL). Extract the aqueous layer with Et2O (100 mL), wash the combined ether layers with 40 mL of saturated NaCl, dry (MgSO4), and concentrate to give 1.11 g (4.02 mmol, >99%) of methyl β-(3,4-dichlorophenyl)oxiranepropanoate as a colorless oil.

Workup

  1. extractionExtract the aqueous layer with Et2O (100 mL)
  2. washwash the combined ether layers with 40 mL of saturated NaCl
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-dd872666ce804133a66cc10f7db2f9ab
Source dataset
uspto-grants-1997_12
Patent number
US05696267

Reaction notes

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