Water → HCID 19980234, compound

HRID 1461249Notes

Reaction equation

HRID 1461249 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].Cl[C:9]1[O:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.O>CN(C)C=O>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[O:4][CH2:3][CH2:2][CH2:1][OH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 119862-ChlorobenzoxazoleHCID 24758Sodium hydride

Product 1

HCID 19980234HCID 19980234, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 1,3-propanediol (65 g) in dimethylformamide (60 ml) was added sodium hydride (3.0 g, 60% dispersion in oil) portionwise. The mixture was stirred until effervescence had ceased. A solution of 2-chlorobenzoxazole (11.4 g) in dimethylformamide (30 ml) was added dropwise. The reaction mixture was stirred at room temperature overnight. The mixture was added to water (600 ml) and extracted with ethyl acetate (3×300 ml). The combined organic extracts were washed with water (2×300 ml), brine (2×300 ml), dried (MgSO4), filtered and evaporated to dryness. The title compound was obtained as an oil following chromatography on silica gel in 3% methanol in dichloromethane.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. washThe combined organic extracts were washed with water (2×300 ml), brine (2×300 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-882e19a2bcb3471bb24df25ce735f4ee
Source dataset
uspto-grants-1991_12
Patent number
US05075300

Reaction notes

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