Triethylamine → 1,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

HRID 727187Notes

Reaction equation

HRID 727187 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 14.2 grams (0.090 mole) of 1,4-dioxaspiro[4.5]decan-8-ol and 10.0 grams (0.099 mole) of triethylamine in 100 mL of methylene chloride is cooled to 0° C., and a solution of 7.7 mL (0.099 mole) of methanesulfonyl chloride in 25 mL of methylene chloride is added drop-wise at a rate to maintain the reaction mixture temperature at 0° C. to 5° C. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is then washed with two 75 mL portions of an aqueous 5% sodium bicarbonate solution and then with 75 mL of an aqueous solution saturated with sodium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane

Workup

  1. temperatureto maintain the reaction mixture temperature at 0° C. to 5° C
  2. additionUpon completion of addition
  3. washThe reaction mixture is then washed with two 75 mL portions of an aqueous 5% sodium bicarbonate solution
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-507f88ff81c744d0a5789cdabcff7dbf
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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