Methyl iodide → HCID 66995363, compound

HRID 2041901Notes

Reaction equation

HRID 2041901 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:20])[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1.[H-].[Na+].[CH3:23]I.[Cl-].[Li+]>CN(C)C=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:20][CH3:23])[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:10]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 433294Lithium ChlorideHCID 65920453HCID 65920453, compound

Product 1

HCID 66995363HCID 66995363, compoundYield 134.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-(2,3-difluorophenyl)-3-hydroxyazetidine-1-carboxylate (1.1 g, 3.86 mmol) in N,N-dimethylformamide (15 mL), was added sodium hydride (60% dispersion in mineral oil, 0.31 g, 7.7 mmol). The mixture was stirred for 20 min and methyliodide (0.29 mL, 4.63 mmol) was added. The mixture was stirred for 30 min, aqueous lithium chloride (50 ml, 5%) was added and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic phase was dried (Na2SO4), filtered and evaporated to give the title compound (1.55 g). MS m/z (rel. intensity, 70 eV) 299 (M+, 1), 223 (21), 169 (62), 140 (49), 57 (bp).

Workup

  1. stirringThe mixture was stirred for 30 min
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-23b7bf3e7d664ded99bc0eb9940db4c7
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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