1,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate → HCID 86609535, compound

HRID 1865471Notes

Reaction equation

HRID 1865471 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].CS(O[CH:11]1[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][CH2:12]1)(=O)=O>CS(C)=O.[Cl-].[Na+].O>[C:1](=[S:3])([O:4][CH:11]1[CH2:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][CH2:12]1)[CH3:2]

Participants

5

Reactant 2

HCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonateHCID 23670855Potassium ethanethioate

Product 1

HCID 86609535HCID 86609535, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

Potassium thioacetate (21.39 g, 187 mmol) was added to a stirred mixture of 1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate (29.5 g, 125 mmol) in DMSO (31.2 ml) and the mixture was heated at 40° C. for 24 h. The mixture was cooled, brine was added and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with brine, dried, and evaporated. The residue was purified by column chromatography on silica gel using a Biotage 65i cartridge, eluting with EtOAc/isohexane to give 1,4-dioxaspiro[4.5]dec-8-yl ethanethioate (17.5 g, 81 mmol, 64.8% yield) as a red oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic fractions were washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel using a Biotage 65i cartridge
  7. washeluting with EtOAc/isohexane

Sources & evidence

ORD record
ord-e66aaddad75d49ba994da6194cf7b440
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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