Hydrochloric Acid → HCID 18314750, compound

HRID 362570Notes

Reaction equation

HRID 362570 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:10]=2)[C:5]1=O.Cl>O1CCCC1.CO>[CH3:3][C:4]1[CH2:12][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[C:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:10]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18314753HCID 18314753, compound

Product 1

HCID 18314750HCID 18314750, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2.4 g (62 mmol) of sodium borohydride were added to a solution of 8.3 g (41 mmol) of 1 in 50 ml of tetrahydrofuran/methanol (2:1), and the mixture was stirred at room temperature for 16 hours. 50 ml of conc. aqueous HCl were subsequently added, and the mixture was extracted 3 times with 50 ml of diethyl ether in each case. The combined organic phases were dried (MgSO4) and freed from solvent on a rotary evaporator. The residue was taken up in 100 ml of toluene, 0.4 g of p-toluenesulfonic acid was added, and the mixture was refluxed for 2 hours. The reaction mixture was washed twice with 50 ml of saturated aqueous NaHCO3 solution in each case and freed from solvent on a rotary evaporator. The residue was purified by chromatography on 400 g of silica gel (hexane), giving 7.17 g (95%) of 2 as a colorless oil.

Workup

  1. extractionthe mixture was extracted 3 times with 50 ml of diethyl ether in each case
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. customfreed from solvent on a rotary evaporator
  4. addition0.4 g of p-toluenesulfonic acid was added
  5. temperaturethe mixture was refluxed for 2 hours
  6. washThe reaction mixture was washed twice with 50 ml of saturated aqueous NaHCO3 solution in each case
  7. customfreed from solvent on a rotary evaporator
  8. customThe residue was purified by chromatography on 400 g of silica gel (hexane)

Sources & evidence

ORD record
ord-3d52e2981e794a47b052f0fcf729f1a9
Source dataset
uspto-grants-1999_02
Patent number
US05869584

Reaction notes

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