Water → 6-(Trifluoroacetamido)-1-hexanol

HRID 2066375Notes

Reaction equation

HRID 2066375 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[F:9][C:10]([F:17])([F:16])[C:11](OCC)=[O:12].O>ClCCl>[F:9][C:10]([F:17])([F:16])[C:11]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 9794Ethyl trifluoroacetateHCID 199606-Amino-1-hexanol

Product 1

HCID 36276076-(Trifluoroacetamido)-1-hexanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-aminohexanol (11.7 g; 100 mmol) is dissolved in dry dichloromethane (100 mL) and drop wise added ethyl trifluoroacetate (15 g; 105 mmol) in dry dichloromethane (50 mL) (˜30 min), and the mixture is stirred overnight. Water (10 ml) is added, and the mixture is stirred for 30 min. The solution is washed with water (2×100 mL), dried (Na2SO4), and concentrated. The residue is redissolved in acetonitrile (100 μL) and concentrated. The residue is placed on vacuum overnight, and a white crystalline solid is obtained. Yield 19 g.

Workup

  1. stirringthe mixture is stirred for 30 min
  2. washThe solution is washed with water (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe residue is redissolved in acetonitrile (100 μL)
  6. concentrationconcentrated
  7. customis placed on vacuum overnight
  8. customa white crystalline solid is obtained

Sources & evidence

ORD record
ord-e12b45d1c0064b6499d8d90420df1902
Source dataset
uspto-grants-2012_10
Patent number
US08293684B2

Reaction notes

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