Sodium borohydride → HCID 13723992, compound

HRID 225365Notes

Reaction equation

HRID 225365 reaction equation
[BH4-].[Na+].[CH:3]1([CH2:8][C:9](=[O:13])/[CH:10]=[CH:11]/[I:12])[CH2:7][CH2:6][CH2:5][CH2:4]1>C1C=CC=CC=1>[CH:3]1([CH2:8][CH:9]([OH:13])/[CH:10]=[CH:11]/[I:12])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23329959HCID 23329959, compound

Product 1

HCID 13723992HCID 13723992, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 7.1 g. of sodium borohydride in 60 ml. of absolute alcohol, stirred in an ice bath under nitrogen atmosphere, is added dropwise, over a period of about 2 hours, a solution containing 87 g. of 4-cyclopentyl-1-iodo-trans-buten-3-one (Example 178) in 160 ml. of absolute alcohol. The temperature is maintained at 5°-10° C. The solution is poured into 850 ml. of ice water and the resulting mixture is extracted three times with ether. The combined extracts are washed with dilute sodium bisulfite solution, saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 81 g. of yellow oil. Column chromatography on a column of 1 kg. of silica gel using benzene as elute gives 75 g. (88%) of oily product.

Workup

  1. additionis added dropwise, over a period of about 2 hours
  2. additiona solution containing 87 g
  3. temperatureThe temperature is maintained at 5°-10° C
  4. additionThe solution is poured into 850 ml
  5. extractionof ice water and the resulting mixture is extracted three times with ether
  6. washThe combined extracts are washed with dilute sodium bisulfite solution, saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customto give 81 g
  9. washas elute
  10. customgives 75 g

Sources & evidence

ORD record
ord-4c7b46c10c4348849e028dd0c7bd18ac
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Reaction notes

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