Ethyl trifluoroacetate → 4-(N-Methyl-trifluoroacetamido)-1-butanol

HRID 565404Notes

Reaction equation

HRID 565404 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[F:8][C:9]([F:16])([F:15])[C:10](OCC)=[O:11]>CO>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][CH2:6][OH:7])[C:10](=[O:11])[C:9]([F:16])([F:15])[F:8]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 98339374-(Methylamino)butan-1-ol

Product 1

HCID 105121904-(N-Methyl-trifluoroacetamido)-1-butanolYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 250 mL round bottom flask, charged with 10.0 g (96.9 mmol) of the amine, 4-methylaminobutanol, in 100 mL of dry methanol, was added 17.5 mL (147 mmol) of ethyl trifluoroacetate. The mixture was stirred at room temperature for 24 hours and then concentrated to afford 18.55 g of the product as a near colorless oil (96%): 1H—NMR (200 MHz, D2O); 3.63 and 3.50 (2t's, 4H), 3.20 and 3.05 (d and s, 3H), and 1.82-1.47 (m, 4H) ppm.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d67331f8c56749db87ac8f5a280e486c
Source dataset
uspto-grants-2001_01
Patent number
US06172045B2

Reaction notes

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