Propanal → HCID 25023069, compound

HRID 1367610Notes

Reaction equation

HRID 1367610 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][O:7][CH2:8][CH:9]([OH:20])[CH2:10][CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16].[CH:21](=O)[CH2:22][CH3:23]>C1(C)C=CC=CC=1>[CH2:22]([CH:23]1[N:4]([CH2:5][CH2:6][O:7][CH2:8][CH:9]([OH:20])[CH2:10][CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH2:3][CH2:2][O:1]1)[CH3:21]

Participants

4

Reactant 2

HCID 527PropanalHCID 25023068HCID 25023068, compound

Product 1

HCID 25023069HCID 25023069, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 10 mL flask containing 1-[2-(2-hydroxy-ethylamino)-ethoxy]-6-propyl-nonan-2-ol (510 mg, 1.76 mmol, 1 eq.) in toluene (3 mL) was added dropwise at room temperature propionaldehyde (0.14 mL 1.85 mmol, 1.05 eq., d=0.798) before heating to reflux with a Dean-Stark trap for 2 h. The reaction was cooled to room temperature and concentrated to afford the title compound as 2 stereoisomers (50:50) (580 mg, 100% yield). 1H NMR (CDCl3, 400 MHz) d?(ppm): 4.09-4.03 (m, H); 3.92-3.81 (m, 2H); 3.81-3.73 (m, H); 3.73-3.50 (m, 2H+2H); 3.35-3.21 (m, 2H); 2.92-2.74 (m, 2H); 2.72-2.63 (m, H); 2.62-2.52 (m, H); 1.69-1.14 (m, 15H+2H); 0.96 (m, 3H); 0.87 (t, J=7.0 Hz, 6H). 13C NMR (CDCl3, 129.9 MHz) d?(ppm): 98.0; 97.9; 76.1; 75.7; 70.6 (2C); 70.2 (2C); 64.2 (2C); 53.2; 53.1; 52.6 (2C); 36.9 (2C); 36.0 (2C+2C); 33.7 (2C); 33.6; 33.5; 26.9; 26.8; 22.7 (2C); 19.8 (2C+2C); 14.5 (2C+2C); 9.2 (2C).

Workup

  1. temperaturebefore heating
  2. temperatureto reflux with a Dean-Stark trap for 2 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6d733c4d502d4addb37e29c54224b2b5
Source dataset
uspto-grants-2011_02
Patent number
US07893258B2

Reaction notes

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