Diethyl Ether → L 698680

HRID 2081538Notes

Reaction equation

HRID 2081538 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13](=[O:29])[NH:14][C:15]([CH2:20][O:21]CC2C=CC=CC=2)=[C:16]([CH2:18][CH3:19])[CH:17]=1.B(Br)(Br)Br.CCCCCC.C(OCC)C>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13](=[O:29])[NH:14][C:15]([CH2:20][OH:21])=[C:16]([CH2:18][CH3:19])[CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 19769118HCID 19769118, compoundHCID 19780039HCID 19780039, compound

Product 1

HCID 126544L 698680

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[2-(benzoxazol-2-yl)ethyl]-5-ethyl-6-benzyloxymethyl-2(1H)-pyridinone (198 mg, 0.51 mmol) in dry methylene chloride (6 mL) was cooled in an ice/acetone bath and 1M boron tribromide/hexane (1.5 mL, 1.5 mmol) was added dropwise to give a white precipitate. This suspension was stirred for one hour and then the reaction was quenched by addition of saturated aqueous NaHCO3 (10 mL). After stirring for 0.5 hours, the product was extracted into CH2Cl2, dried, filtered and the solvent evaporated to give a solid. Trituration with diethyl ether gave product as a tan solid. Recrystallization from ethyl acetate afforded a light yellow solid with m.p. of 155°-156° C.

Workup

  1. customto give a white precipitate
  2. customthe reaction was quenched by addition of saturated aqueous NaHCO3 (10 mL)
  3. stirringAfter stirring for 0.5 hours
  4. extractionthe product was extracted into CH2Cl2
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customto give a solid
  9. customRecrystallization from ethyl acetate
  10. customafforded a light yellow solid with m.p. of 155°-156° C.

Sources & evidence

ORD record
ord-56f578cb20934d468aac3ea716c24fc1
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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