Chloromethyl Methyl Ether → 2-Chloro-n-ethyl-n-(methoxymethyl)-6-(trimethylsilyl)benzamide

HRID 356349Notes

Reaction equation

HRID 356349 reaction equation
C([Mg]Cl)(C)(C)C.[Cl:7][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]([Si:19]([CH3:22])([CH3:21])[CH3:20])[C:9]=1[C:10]([NH:12][CH2:13][CH3:14])=[O:11].[CH3:23][O:24][CH2:25]Cl>C1COCC1>[Cl:7][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]([Si:19]([CH3:21])([CH3:20])[CH3:22])[C:9]=1[C:10]([N:12]([CH2:13][CH3:14])[CH2:23][O:24][CH3:25])=[O:11]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 186303792-Chloro-n-ethyl-6-(trimethylsilyl)benzamideHCID 178418310HCID 178418310, compound

Product 1

HCID 186303292-Chloro-n-ethyl-n-(methoxymethyl)-6-(trimethylsilyl)benzamideYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2M THF solution of tert-butylmagnesium chloride (2.5 mL, 5 mmol) was added to an ice water cooled solution of the compound of Example 45 (1.28 g, 5 mmol) in THF (25 mL). Chloromethyl methyl ether (0.44 g, 5.5 mmol) was then added and the reaction mixture was stirred at ambient temperature for 1 h and then partitioned between water and ethyl acetate. The organic solution was dried (MgSO4), concentrated, and purified by RC with 1:9 ethyl acetate/hexanes to afford 0.80 g of the title compound as a colorless oil, a 53% yield.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by RC with 1:9 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-87b867c68a2f4234920b593026ce7fe1
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

Loading…