Propanal → HCID 25023069, compound

HRID 419782Notes

Reaction equation

HRID 419782 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 2h. 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; 78,1; 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 2h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-07fa8771732d4099925f718c9faff1d8
Source dataset
uspto-grants-2012_01
Patent number
US08093398B2

Reaction notes

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