Sodium borohydride → HCID 21521019, compound

HRID 918439Notes

Reaction equation

HRID 918439 reaction equation
[BH4-].[Na+].[N:3]1([CH:9]2[CH2:13][C:12]3[C:14]([O:35][CH3:36])=[C:15]([C:23](=[O:34])[CH:24]=[CH:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[C:16]([O:20][CH2:21][CH3:22])=[C:17]([O:18][CH3:19])[C:11]=3[O:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>N1C=CC=CC=1>[N:3]1([CH:9]2[CH2:13][C:12]3[C:14]([O:35][CH3:36])=[C:15]([CH:23]([OH:34])[CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[C:16]([O:20][CH2:21][CH3:22])=[C:17]([O:18][CH3:19])[C:11]=3[O:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68137773HCID 68137773, compound

Product 1

HCID 21521019HCID 21521019, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

65.2g of pyridine, 2ml of concentrated soda and then 31.3g of powdered sodium borohydride is added to a solution in 500ml of 96° alcohol of 77g of piperidino-6-ethoxy-5-p-methoxycinnamoyl-4,7-dimethoxy-2,3-dihydrobenzofuran obtained in the preceding stage, over a period of 10 to 15 minutes. The mixture is refluxed for 7 hours, the solvents removed, the residue is dissolved in water extracted with ethyl acetate, washed with water, dried over sodium sulphate and evaporated to dryness. The crude product obtained is recrystallised from 96° alcohol.

Workup

  1. customobtained in the preceding stage, over a period of 10 to 15 minutes
  2. temperatureThe mixture is refluxed for 7 hours
  3. customthe solvents removed
  4. dissolutionthe residue is dissolved in water
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-7d6522e2b04546c0bb4acb70d3c09d1d
Source dataset
uspto-grants-1976_07
Patent number
US03971793

Reaction notes

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