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

HRID 40986

Reaction equation

HRID 40986 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.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[CH3:12][S:13]([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:15])=[O:14]

Participants

4

Reactant 2

HCID 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 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

1,4-Dioxaspiro[4.5]decan-8-ol (0.40 g, 0.0025 mol) was dissolved in chloroform (10.0 mL) and the resulting mixture was cooled at 0° C. To the mixture was added TEA (0.49 mL, 0.0035 mol) and methanesulfonyl chloride (0.23 mL, 0.0030 mol) and this mixture was stirred at 0° C. for 2 hours. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, and saturated NaCl, then dried (MgSO4) and concentrated in vacuo. The crude product was used in the next reaction without further purification.

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic extracts were washed with water, and saturated NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-4d23c9e92ae44147a899cda23b71c32d
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Linked notes

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