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

HRID 1896855Notes

Reaction equation

HRID 1896855 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]>C1COCC1.O>[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

6

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 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,4-dioxaspiro[4.5]decan-8-ol (1 g, 6.32 mmol) and triethylamine (1.3 mL, 9.48 mmol) taken in anhydrous THF and treated with methanesulfonyl chloride (0.73 mL, 9.48 mmol). Stirred for 18 h. Diluted with water and extracted with EtOAc. The ethyl acetate layer washed with sat NaCl, dried over Na2SO4 and evaporated to give the expected product. Used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe ethyl acetate layer washed
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d7a3d9cd0f1842508332c2c2824ab5a8
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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