Sodium borohydride → HCID 13723992, compound

HRID 1448629Notes

Reaction equation

HRID 1448629 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 7 g. of 4-cyclopentyl-1-iodo-1-trans-buten-3-one (Example 33) in 160 ml. of absolute alcohol. The temperature is maintained at 5°-10° C. The solution is poured into 850 ml. of iced 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 gives 75 g. (88%) of oily product.

Workup

  1. additionis added dropwise, over a period of about 2 hours
  2. additiona solution containing 7 g
  3. temperatureThe temperature is maintained at 5°-10° C
  4. additionThe solution is poured into 850 ml
  5. extractionof iced 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. customgives 75 g

Sources & evidence

ORD record
ord-abd99f0d7b33427c9eb3ad2d62a06dc1
Source dataset
uspto-grants-1979_12
Patent number
US04180677

Reaction notes

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