Water → HCID 11120552, compound

HRID 1620785Notes

Reaction equation

HRID 1620785 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.S(O[Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])(OC(F)(F)F)(=O)=O.O>ClCCl>[O:1]1[C:5]2([CH2:6][CH2:7][C:8]([O:11][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])=[CH:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 86678943HCID 86678943, compound

Product 1

HCID 11120552HCID 11120552, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-one (11.6 g) in dichloromethane (200 mL) were added dropwise triethylamine (20.7 mL) and trifluoromethyl tri(propan-2-yl)silyl sulfate (25.0 g). The reaction mixture was stirred at room temperature so for 1 hr, and ice-cooled water was added. The organic layer was separated, washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (22.0 g).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-ff1754c165814ece8533542c8bd06767
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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