Triethylamine → HCID 86616918, compound

HRID 1157101Notes

Reaction equation

HRID 1157101 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][C@@H:4]([OH:6])[CH3:5].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(OCC)(=O)C>[CH3:15][S:16]([O:7][CH2:1][CH2:2][CH2:3][C@@H:4]([O:6][S:16]([CH3:15])(=[O:18])=[O:17])[CH3:5])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7271800(S)-1,4-pentanediol

Product 1

HCID 86616918HCID 86616918, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A solution containing 2.5 g (24 mmol) of (S)-1,4-pentanediol produced in Example 3, 7.3 g (72 mmol) of triethylamine, and 30 mL of ethyl acetate was cooled to 5° C. Subsequently, 6.6 g (58 mmol) of methanesulfonyl chloride was added to the solution, and the solution was stirred for one hour. The solution was washed by adding 15 mL of a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was further washed with 15 mL of water, and was dried over anhydrous magnesium sulfate. The solvent was then distilled off under a reduced pressure. Thus, (S)-1,4-bis(methanesulfonyloxy)pentane was obtained as a light yellow oily substance (6.1 g, yield; 98%).

Workup

  1. washThe solution was washed
  2. additionby adding 15 mL of a saturated aqueous solution of sodium hydrogencarbonate
  3. washThe organic layer was further washed with 15 mL of water
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under a reduced pressure

Sources & evidence

ORD record
ord-6fef562ccffe4b36acae5c717b9bc0ab
Source dataset
uspto-grants-2010_10
Patent number
US07807426B2

Reaction notes

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