7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane → 2-(1-Methylethyl)tetrahydro-4H-thiopyran-4-one

HRID 656045Notes

Reaction equation

HRID 656045 reaction equation
[CH3:1][CH:2]([CH:4]1[S:13][CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5]1)[CH3:3]>C(O)(=O)C.Cl>[CH3:1][CH:2]([CH:4]1[CH2:5][C:6](=[O:7])[CH2:11][CH2:12][S:13]1)[CH3:3]

Participants

4

Reactant 1

HCID 593327327-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane

Product 1

HCID 593325652-(1-Methylethyl)tetrahydro-4H-thiopyran-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane was dissolved in acetic acid (50 mL) and 2 N aqueous hydrochloric acid (70 mL). After being stirred at room temperature for 15 h, the mixture was extracted with ether (300 mL), and the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL), and finally with water (2×50 mL). The dried (Na2SO4) solution was evaporated, and the residue purified by column chromatography on silica, giving 3.6 (22% over two steps) of the title compound.

Workup

  1. extractionthe mixture was extracted with ether (300 mL)
  2. extractionthe ether extract
  3. washwashed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL)
  4. dry with materialThe dried (Na2SO4) solution
  5. customwas evaporated
  6. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-df77043e465e4c95a5ae0d070b5d35dd
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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