1-Octanol → HCID 22506523, compound

HRID 985363Notes

Reaction equation

HRID 985363 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24]>O>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([C:8](=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 8471TriethylamineHCID 3787675Pyridine-2-sulfonyl Chloride

Product 1

HCID 22506523HCID 22506523, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.0 mL of anhydrous triethylamine (23.04 mmol, 30 equiv.) at 0° C. was added 1-octanol (0.10 g 0.77 mmol, 1 equiv.) followed by the addition of 2-pyridylsulfonyl chloride in one portion. The mixture was kept at 0° C. for 3 hours followed by the addition of water (5 mL). The resulting mixture was extracted with diethyl ether (3×50 mL), then the organic extracts were combined and washed with aqueous NaHCO3 solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. Column chromatography (2% EtOAc/Hex) afforded 15 (99%): 1H NMR (CDCl3, 400 MHz) δ 8.68 (d, J=7.0 Hz, 1H, ArH), 7.94 (p, J=8.8 Hz, 2H, ArH), 7.54 (t, J=6.4 Hz, 1H, ArH), 4.26 (t, J=6.7 Hz, 2H, CH2OSO2R), 1.61 (p, J=7.9 Hz, 2H), 1.13 (m, 10H), 0.76 (t, J=7.0 Hz, 3H); MALDI-FTMS 294.1130 (C13H21NO3S+Na+ requires 294.1134).

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether (3×50 mL)
  2. washwashed with aqueous NaHCO3 solution (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fde9a9a3ee654a6e975fdb9ae4b8861d
Source dataset
uspto-grants-2005_03
Patent number
US06872574B2

Reaction notes

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