Dimethyl Sulfoxide → spiro[4.5]decan-7-one

HRID 1631853Notes

Reaction equation

HRID 1631853 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]1[C:15]2([CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]2)[CH2:14][CH2:13][CH2:12]1.[Cl-].[NH4+]>C(N(CC)CC)C.C(Cl)Cl>[CH2:11]1[C:15]2([CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]2)[CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 24974730HCID 24974730, compound

Product 1

HCID 10888101spiro[4.5]decan-7-oneYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-70 °C

Procedure

With stirring under nitrogen atmosphere at −70° C., 12.0 g of dimethyl sulfoxide was added to a mixture of 14.4 g of oxalyl chloride and 100 ml of methylene chloride. Stirring was continued for 10 minutes. Below −55° C., a mixture of 8.72 g of 7-spiro[4.5]decanol and 20 ml of methylene chloride was added dropwise thereto, followed by stirring for 30 minutes at −70° C. After 50 g of triethylamine was added, the mixture was warmed up to −5° C. while stirring. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, followed by ordinary work-up of extraction, washing and drying, and purification by silica gel chromatography. There was obtained 8.22 g (yield 96%) of 7-spiro[4.5]decanone. This compound was found to have identical spectroscopic characteristics with the former compound.

Workup

  1. stirringStirring
  2. additionwas added dropwise
  3. stirringby stirring for 30 minutes at −70° C
  4. temperaturethe mixture was warmed up to −5° C.
  5. stirringwhile stirring
  6. extractionfollowed by ordinary work-up of extraction
  7. washwashing
  8. customdrying
  9. custompurification by silica gel chromatography

Sources & evidence

ORD record
ord-aa4a482ddd8c46658d60f1be7c163d6c
Source dataset
uspto-grants-2014_07
Patent number
US08791288B2

Reaction notes

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