Methanol → HCID 10154867, compound

HRID 842119Notes

Reaction equation

HRID 842119 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[O:6][C:7]2[C:13]([CH2:14][CH2:15][CH2:16][O:17]S(C)(=O)=O)=[CH:12][C:11]([Cl:22])=[CH:10][C:8]=2[N:9]=1.[CH3:27][O-].[Na+].CO.[Na]>O>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[O:6][C:7]2[C:13]([CH2:14][CH2:15][CH2:16][O:17][CH3:27])=[CH:12][C:11]([Cl:22])=[CH:10][C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22618326HCID 22618326, compound

Product 1

HCID 10154867HCID 10154867, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Chlorobenzyl)-5-chloro-7-(3-methanesulfonyloxy-1-propyl)-benzoxazole was stirred overnight with a solution of sodium methoxide prepared from methanol (100 ml) and sodium (2.7 g, 0.118 mol). The reaction mixture was diluted with water and extracted with dichloromethane. The dichloromethane solution was washed with water and evaporated to give the crude product (10 g). The crude product was purified over flash chromatography silica gel and eluted with 30% dichloromethane/hexane. The effluent was collected in 200 ml fractions. Fractions 1-7 contained an impurity (7.1 g); fractions 8-11 were collected (1.8 g) and recrystallized three times from hexane to give the title compound (0.4 g), mp 49-51°.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane solution was washed with water
  3. customevaporated
  4. customto give the crude product (10 g)
  5. customThe crude product was purified over flash chromatography silica gel
  6. washeluted with 30% dichloromethane/hexane
  7. customThe effluent was collected in 200 ml fractions
  8. customfractions 8-11 were collected (1.8 g)
  9. customrecrystallized three times from hexane

Sources & evidence

ORD record
ord-846673dc9c834545bde4dc90ee804e0d
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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