1-Octanol → HCID 22506522, compound

HRID 985365Notes

Reaction equation

HRID 985365 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].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([C:8](=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 22506522HCID 22506522, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triethylamine (0.12 g, 1.15 mmol, 1.5 equiv.) in dichloromethane (3 mL) was added octanol (0.10 g, 0.77 mmol, 1.0 equiv.) at 0° C. followed by the addition of methanesulfonyl chloride (0.10 g, 0.85 mmol, 1.1 equiv.), over a period of 5 minutes. After 30 minutes at 0° C., the reaction mixture was diluted in dichloromethane (50 mL) and extracted with ice cold water (50 mL), ice cold 10% aqueous HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and with saturated aqueous NaCl (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 17 (97%): 1H NMR (CDCl3, 400 MHz) δ 4.21 (t, J=6.5 Hz, 2H, CH2OSO2Me), 2.99 (s, 3H, CH3SO3), 1.77 (p, J=6.7 Hz, 2H), 1.35 (m, 10H), 0.87 (t, J=6.1 Hz, 3H).

Workup

  1. extractionextracted with ice cold water (50 mL), ice cold 10% aqueous HCl (50 mL), saturated aqueous NaHCO3 (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c92eb632242c4152b2131b48af58153f
Source dataset
uspto-grants-2005_03
Patent number
US06872574B2

Reaction notes

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