Boron Trichloride → 4-(4-Chlorophenyl)-2-oxazolemethanol

HRID 623217Notes

Reaction equation

HRID 623217 reaction equation
B(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([CH2:17][O:18]CC)[O:15][CH:16]=2)=[CH:8][CH:7]=1>ClCCl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]([CH2:17][OH:18])[O:15][CH:16]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 21290687HCID 21290687, compound

Product 1

HCID 212906854-(4-Chlorophenyl)-2-oxazolemethanolYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

181 ml of a 1M solution of boron trichloride in dichloromethane was added dropwise to a stirred solution of 21.5 g (90.5 mmol) of 4-(4-chlorophenyl)-2-ethoxymethyl-oxazole in 100 ml of dichloromethane. The temperature of the mixture was held below 10° C. during the addition by cooling with ice. After completion of the addition the mixture was stirred at room temperature for 2 hours and then poured on to 500 ml of ice/water. The dichloromethane phase was separated and the aqueous phase was extracted with 100 ml of dichloromethane. The combined dichloromethane extracts were washed with saturated sodium hydrogen carbonate solution, dried over sodium sulphate, filtered and evaporated. Recrystallization of the residue from toluene yielded 15.7 g (83%) of 4-(4-chlorophenyl)-2-oxazolemethanol of melting point 68°-71.5° C.

Workup

  1. additionThe temperature of the mixture was held below 10° C. during the addition
  2. temperatureby cooling with ice
  3. additionAfter completion of the addition the mixture
  4. customThe dichloromethane phase was separated
  5. extractionthe aqueous phase was extracted with 100 ml of dichloromethane
  6. washThe combined dichloromethane extracts were washed with saturated sodium hydrogen carbonate solution
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customRecrystallization of the residue from toluene

Sources & evidence

ORD record
ord-b4fbc8ab92dd4fb183a50972e933832c
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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