Hydrochloric Acid → HCID 18953960, compound

HRID 1491672Notes

Reaction equation

HRID 1491672 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][OH:16])[O:11][CH:12]=2)=[CH:4][CH:3]=1.CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl>ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH:15]=[O:16])[O:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14812Phosphorus oxide (P4O10)HCID 9837611HCID 9837611, compound

Product 1

HCID 18953960HCID 18953960, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-[4-(4-chlorophenyl)-2-oxazolyl]propanol (1.0 g) in dichloromethane (10 ml) were added dimethylsulfoxide (0.6 ml) and phosphoric anhydride (1.1 g) in that order. After stirring for 10 minutes at room temperature, the resultant was cooled to 0° C., to which triethylamine (2 ml) was added. The mixture was stirred for 40 minutes at room temperature, poured into 2N-HCl and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over MgSO4 and distilled to remove the solvent. The oily residue was subjected to a silica gel column chromatography. Crystals of 3-[4-(4-chlorophenyl)-2-oxazolyl]propanal (0.698 g, 70%) were obtained from the fraction eluted with ethyl acetate-hexane (1:3, V/V). Recrystallization from hexane gave colorless prism crystals of mp 41°-42° C.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 40 minutes at room temperature
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane layer was washed with water
  5. dry with materialdried over MgSO4
  6. distillationdistilled
  7. customto remove the solvent

Sources & evidence

ORD record
ord-080b23155645472ba7b60575f4763638
Source dataset
uspto-grants-1994_12
Patent number
US05371098

Reaction notes

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