Hydrochloric Acid → HCID 22009803, compound

HRID 322251Notes

Reaction equation

HRID 322251 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O1CCCC1.[ClH:31]>O.C(O)C>[Cl:31][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH2:14][C:12]2[N:13]=[C:9](/[CH:8]=[CH:7]/[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:10][CH:11]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 22009655HCID 22009655, compound

Product 1

HCID 22009803HCID 22009803, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-[2-[(E)-2-phenylethenyl]-4-oxazolyl methoxy]benzaldehyde (5.00 g), sodium borohydride (620 mg), tetrahydrofuran (50 ml) and ethanol (50 ml) was stirred for 16 hours at room temperature. The reaction mixture was poured into water and acidified with 2N hydrochloric acid. The resulting precipitate was collected by filtration and dried, which was suspended in chloroform (50 ml). To the suspension was added thionyl chloride (2.00 g). The mixture was stirred for one hour at room temperature. The reaction mixture was concentrated, to which was added ethyl acetate, followed by washing with saturated aqueous sodium hydrogencarbonate and water. The ethyl acetate layer was separated and dried (MgSO4). The solvent was distilled off to leave crystals, followed by recrystallization from chloroform-isopropyl ether to give 4-(4-chloromethylphenoxymethyl)-2-[(E)-2-phenylethenyl]oxazole (3.25 g, 61%) as colorless prisms, mp 116-117° C.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried
  3. additionTo the suspension was added thionyl chloride (2.00 g)
  4. stirringThe mixture was stirred for one hour at room temperature
  5. concentrationThe reaction mixture was concentrated, to which
  6. additionwas added ethyl acetate
  7. washby washing with saturated aqueous sodium hydrogencarbonate and water
  8. customThe ethyl acetate layer was separated
  9. dry with materialdried (MgSO4)
  10. distillationThe solvent was distilled off
  11. customto leave crystals
  12. customfollowed by recrystallization from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-00a6daf9745b413d8391f1fab5513ed2
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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