Sodium borohydride → HCID 13690970, compound

HRID 2290773Notes

Reaction equation

HRID 2290773 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:17])[CH2:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([CH2:15][Cl:16])[N:11]=2)=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:2]=[CH:3][C:4]([CH:7]([OH:17])[CH2:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([CH2:15][Cl:16])[N:11]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13690942HCID 13690942, compound

Product 1

HCID 13690970HCID 13690970, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.03 g of 5-[3-(4-biphenylyl)-3-oxopropyl]-3-chloromethyl-1,2,4-oxadiazole obtained in Example 3 in 100 ml of ethanol was added 0.12 g of sodium borohydride. After stirring for 10 minutes at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was treated with ice-water and extracted with chloroform. The organic phase was washed with water, dried over sodium sulfate and evaporated to give 1.0 g of 5-[3-(4-biphenylyl)-3-hydroxypropyl]-3-chloromethyl-1,2,4-oxadiazole, m.p. 48°-49° C.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was treated with ice-water
  3. extractionextracted with chloroform
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-56ed1a60574d40b594c2d97844036044
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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