Triethylamine → 4-Methanesulfonyloxyheptane

HRID 902226Notes

Reaction equation

HRID 902226 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([OH:8])[CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:8][CH:4]([CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2][CH3:1])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115134-HeptanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 121363934-Methanesulfonyloxyheptane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of 834 mg (7.19 mmol) of 4-heptanol in 35 mL of CH2Cl2 was added 1.5 mL of triethylamine. Next, 0.7 mL (9 mmol) of methanesulfonyl chloride was added, dropwise, over 1 minute. The mixture was stirred at 0° C. for 30 minutes, then extracted with H2O (1×15 mL), 5% NH4OH (2×15 mL), 1M HCl (2×15 mL), and brine (1×15 mL), dried over MgSO4, filtered, and concentrated to an oil. Yield 1.31 g (94%). 1H NMR (300 MHz, CDCl3) d 0.96 (t, 6, J=9), 1.43 (m, 4), 1.64 (m, 4), 3.00 (s, 3), 4.73 (quintet, 1 J=5).

Workup

  1. extractionextracted with H2O (1×15 mL), 5% NH4OH (2×15 mL), 1M HCl (2×15 mL), and brine (1×15 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-d2e4cd17d9504bba9692be24ea92a44f
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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