Salicylaldehyde → HCID 23136275, compound

HRID 1678579Notes

Reaction equation

HRID 1678579 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH:10]1(Br)[CH2:14][CH2:13][CH2:12][CH2:11]1.[H-].[Na+].[BH4-].[Na+]>CN(C=O)C.CO.O>[CH:10]1([O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH2:1][OH:9])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

8

Reactant 4

HCID 6998SalicylaldehydeHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 4311764Sodium borohydride

Product 1

HCID 23136275HCID 23136275, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Salicylaldehyde (1.0 g, 8.2 mmol) was dissolved in DMF (10 mL), cyclopentyl bromide (1.76 mL, 16.4 mmol) and sodium hydride (394 mg, 9.8 mmol) were added thereto, and then the mixture was stirred at room temperature for 2 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 90:10) to give an oily matter. The resulting oily matter was dissolved in methanol (10 mL), sodium borohydride (620 mg, 16.4 mmol) was added thereto, and then the mixture was stirred at room temperature for 2 hours. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30) to give the title compound (349 mg, yield 25%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 90:10)
  5. customto give an oily matter
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-e1c98886a5dd43fcb9d85ee6f6b9c955
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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