Ethyl trifluoroacetate → N-(4-Hydroxybutyl)trifluoroacetamide

HRID 1484484Notes

Reaction equation

HRID 1484484 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>>[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9]

Participants

3

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 258684-Amino-1-butanol

Product 1

HCID 3586224N-(4-Hydroxybutyl)trifluoroacetamide

Conditions

Temperature
0 °C

Procedure

Ethyl trifluoroacetate (3.3 mL; 28 mmol) was added dropwise to cooled (0° C.) 4-amino-1-butanol (2.0 g; 22.4 mmol). The mixture was stirred for 2 h at 0° C. and evaporated. The clear liquid was dried on the high vacuum. The product was obtained in a yield of 4.1 g (99%). 1H-NMR (500 MHz, CDCl3): δ=1.61-1.67 ppm (m, 2H), 1.68-1.74 ppm (m, 2H), 2.31 (bs, 1H), 3.38 ppm (dt, 2H), 3.72 ppm (t, 2H), 7.40 ppm (bs, 1H); 13C-NMR (500 MHz, CDCl3): δ=26.02, 29.70, 40.01, 62.48, 116.20 ppm (q, J=1144.0 Hz), 157.66 ppm (q, J=146.5 Hz). HRMS [+Scan]; calculated m/z for C6H11NO2F3 186.0747; observed mass: 186.0741.

Workup

  1. customevaporated
  2. customThe clear liquid was dried on the high vacuum
  3. customThe product was obtained in a yield of 4.1 g (99%)

Sources & evidence

ORD record
ord-f8671099b2a44f87b0409ba807d2be17
Source dataset
uspto-grants-2016_08
Patent number
US09422232B2

Reaction notes

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