Triethylamine → Oxan-4-ylmethyl methanesulfonate

HRID 744110Notes

Reaction equation

HRID 744110 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C1COCC1>[CH3:16][S:17]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 15166436Oxan-4-ylmethyl methanesulfonateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (IV) (1.25 g, 10.78 mmol) in dry THF (20 mL) at 0° C. under a nitrogen atmosphere was added triethyl amine (2.26 mL, 16.17 mmol) followed by methanesulfonyl chloride (1.0 mL, 12.94 mmol). The ice bath was removed and the reaction mixture was stirred for and additional 2 hours. Sodium bicarbonate (10% aq., 20 mL) was then added to the reaction mixture followed by extraction with ethyl acetate (3×20 mL). Combined organic extracts were then dried over anhydrous potassium carbonate. Filtration, followed by evaporation of solvents on a rotary evaporator yielded the mesylate (V) as a yellow oil (2.01 g, 96% yield).

Workup

  1. customThe ice bath was removed
  2. additionSodium bicarbonate (10% aq., 20 mL) was then added to the reaction mixture
  3. extractionfollowed by extraction with ethyl acetate (3×20 mL)
  4. dry with materialCombined organic extracts were then dried over anhydrous potassium carbonate
  5. filtrationFiltration
  6. customfollowed by evaporation of solvents on a rotary evaporator

Sources & evidence

ORD record
ord-98eeaf22bf70466081a2c4dc1b508a17
Source dataset
uspto-grants-1996_09
Patent number
US05559124

Reaction notes

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