Acetic Acid → HCID 17206777, compound

HRID 1019834Notes

Reaction equation

HRID 1019834 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH:12]=O.C(O)(=O)C.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH2:12][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 691752,4-DimethoxybenzaldehydeHCID 756345-Aminopentan-1-olHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 17206777HCID 17206777, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 5-aminopentan-1-ol (194 mmol), 2,4-dimethoxybenzaldehyde (213 mmol) and acetic acid (213 mmol) in methanol (500 ml) was stirred at 10° C. for 0.5 h. NaBH4 (22 g) was added portionwise at −10° C. and the mixture was stirred for 10 minutes. Then the reaction mixture was allowed to warm to 10° C. and stirred for 1.5 h. Saturated NaHCO3 was added and the mixture was stirred for 0.5 h. The mixture was extracted by CH2Cl2 (3×100 ml). The combined organic phase was washed by saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow oil. Yield: 46 g (69% purity, 65% yield).

Workup

  1. stirringstirred for 1.5 h
  2. stirringthe mixture was stirred for 0.5 h
  3. extractionThe mixture was extracted by CH2Cl2 (3×100 ml)
  4. washThe combined organic phase was washed by saturated brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-6ea4863fbd0f4cb1ad32c0a0a91b82f8
Source dataset
uspto-grants-2014_05
Patent number
US08716293B2

Reaction notes

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