Sodium Hydroxide → HCID 57135362, compound

HRID 1038066Notes

Reaction equation

HRID 1038066 reaction equation
[OH-].[Na+].[I-:3].[CH2:4]([O:7][C:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][N+:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH2:6]>CS(C)=O.O.CCOCC>[I-:3].[CH2:4]([O:7][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:9][N+:10]([CH3:13])([CH3:11])[CH3:12])[CH:5]=[CH2:6].[CH2:17]([O:16][C:14](=[O:15])[C:8]([O:7][CH2:4][CH:5]=[CH2:6])=[CH2:9])[CH3:18]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 86614437HCID 86614437, compound

Product 2

HCID 57135362HCID 57135362, compoundYield 109.1%HCID 86614437HCID 86614437, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

The (2-allyloxy-2,2-bis-ethoxycarbonyl-ethyl)-trimethyl-ammonium iodide was prepared according to a procedure essentially similar to that described in J. Am. Chem. Soc. 1987, 109, 1170-1186, the disclosure of which is incorporated herein by reference thereto. At 0 C, a solution of NaOH (1N, 6 ml) was added into a stirred solution of (2-allyloxy-2,2-bis-ethoxycarbonyl-ethyl)-trimethyl-ammonium iodide (2.1 g) in DMSO and water (9:1, 35 ml) and resulting solution was allowed to stir at room temperature overnight. The reaction mixture was diluted with ether, washed with water three times, brine and dried (MgSO4). After evaporation of solvent, the title compound (431 mg) was obtained.

Workup

  1. customresulting solution
  2. washwashed with water three times, brine
  3. dry with materialdried (MgSO4)
  4. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-4483d0d526614b5490456b1828f9a270
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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