Trifluoromethanesulfonic anhydride → 1-Oxaspiro[4.5]decan-8-one

HRID 2380404Notes

Reaction equation

HRID 2380404 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([CH2:11][CH2:12][CH2:13][OH:14])(O)[CH2:6][CH2:5]2)[O:3]C1.C(N(C(C)C)CC)(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(Cl)Cl>[O:14]1[C:7]2([CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]2)[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 538660308-(3-Hydroxypropyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 132984281-Oxaspiro[4.5]decan-8-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-hydroxypropyl)-4-hydroxy-cyclohexanone ethylene ketal (1.4 g) and diisopropylethylamine (3.37 mL) in methylene chloride (100 mL) at -78° C. was treated with triflic anhydride (1.64 mL). After 30 min the reaction mixture was washed with water, the solvent was dried over magnesium sulfate and removed in vacuo. The residue was dissolved in 30 mL of tetrahydrofuran and 15 mL of 3% HCl. After 5 h at room temperature the reaction mixture was diluted with water and the product was extracted with ether. After drying over magnesium sulfate the solvent was removed in vacuo to afford 1-oxaspiro[4.5]decan-8-one as an oil.

Workup

  1. washAfter 30 min the reaction mixture was washed with water
  2. dry with materialthe solvent was dried over magnesium sulfate
  3. customremoved in vacuo
  4. dissolutionThe residue was dissolved in 30 mL of tetrahydrofuran
  5. additionAfter 5 h at room temperature the reaction mixture was diluted with water
  6. extractionthe product was extracted with ether
  7. dry with materialAfter drying over magnesium sulfate the solvent
  8. customwas removed in vacuo

Sources & evidence

ORD record
ord-7444cfc863b34f3e9552e8dd099abfa9
Source dataset
uspto-grants-1994_11
Patent number
US05367077

Reaction notes

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