Pyridine → HCID 22902160, compound

HRID 1489543Notes

Reaction equation

HRID 1489543 reaction equation
C(OCCBr)(=O)CCCCCCC.[Br:14][CH2:15][CH2:16][CH2:17][OH:18].[C:19](Cl)(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].N1C=CC=CC=1>C1C=CC=CC=1.C(Cl)(Cl)Cl.CO>[C:19]([O:18][CH2:17][CH2:16][CH2:15][Br:14])(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8206Palmitoyl chlorideHCID 123083-Bromo-1-propanolHCID 2298832-bromoethyl octanoate

Product 1

HCID 22902160HCID 22902160, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 21584188Chloroform methanolSolvent

Procedure

This intermediate was prepared in a manner analogous to that of 2-bromoethyl octanoate from 3-bromo-1-propanol (2.53 g, 18 mmol), hexadecanoyl chloride (6.25 g, 22.5 mmol), and pyridine (4 mL) in benzene (50 mL). Silica gel chromatography using chloroform/methanol (9:1) yielded 5.7 g pure product. Yield 69%; liquid; 1H NMR (CDCl3) 0.85-0.95 (t, CH3 (CH2)12), 1.20-1.40 (m, CH3 (CH2)12), 1.55-1.70 (m, CH2 CH2 CO), 2.13-2.23 (m, O CH2 CH2 CH2 Br), 2.28-2.38 (t, CH2 CH2 CO), 3.45-3.50 (t, O CH2 CH2 CH2 Br), 4.35-4.40 (t, O CH2 CH2 CH2 Br).

Sources & evidence

ORD record
ord-8d5e245869844061b3e31eb8b69871b1
Source dataset
uspto-grants-1997_10
Patent number
US05679684

Reaction notes

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