Triethylamine → 7-(Tetrahydropyran-2-yloxy)heptyl methanesulfonate

HRID 329517Notes

Reaction equation

HRID 329517 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][S:2]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 103984241-Heptanol, 7-[(tetrahydro-2H-pyran-2-yl)oxy]-

Product 1

HCID 150972517-(Tetrahydropyran-2-yloxy)heptyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2.32 ml of methanesulfonyl chloride dissolved in 10 ml of benzene was added dropwise, whilst ice-cooling, to a solution of 4.32 g of 7-(tetrahydropyran-2-yloxy)-1-heptanol and 5.56 ml of triethylamine dissolved in 80 ml of benzene. The mixture was stirred at room temperature for 1 hour, after which it was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give 5.86 g of 7-(tetrahydropyran-2-yloxy)heptyl methanesulfonate, as an oil.

Workup

  1. additionwas added dropwise, whilst ice-
  2. washafter which it was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-965ab1cac64e421082060df57d0383c6
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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