Sodium borohydride → HCID 19744741, compound

HRID 2254433Notes

Reaction equation

HRID 2254433 reaction equation
[CH:1](/[C:9]1[O:13][C:12]([C:14](OCC)=[O:15])=[N:11][CH:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-]>C(O)C>[OH:15][CH2:14][C:12]1[O:13][C:9](/[CH:1]=[CH:2]/[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86747107HCID 86747107, compound

Product 1

HCID 19744741HCID 19744741, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

150 mg of ethyl (E)-5-styryloxazole-2carboxylate Yakugaku Zasshi, vol. 91, page 425 (1971)) was suspended in 15 ml of ethanol, and at -10° C., 5 ml of an ethanol solution of 35 mg of sodium borohydride and 123 mg of calcium chloride was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and water and ethyl ether were added to the residue to perform extraction. The organic layer was separated, and then dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give 120 mg (yield 97%) of the captioned compound as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl ether
  2. additionwere added to the residue
  3. extractionextraction
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe desiccant was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed2dd84bb08549fc9a3e6af90a72a7d4
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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