Diisopropylamine → 1,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

HRID 1383760Notes

Reaction equation

HRID 1383760 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1.C1(N[S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1>[O:23]1[C:16]2([CH2:17][CH2:18][C:19]([O:22][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=[CH:20][CH2:21]2)[O:15][CH2:14][CH2:13]1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 516892Sodium BicarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of diisopropylamine (7.6 mL, 54.3 mmol) in 200 mL THF cooled to −78° C. was added n-butyllithium (21.8 mL 2.5 M in hexane, 54.3 mmol) under argon.The solution was stirred for 10 minutes, then a solution of 1,4-cyclohexanedione monoethylene ketal (8.5 g, 54.3 mmol) in 75 mL THF was added slowly. The solution was stirred for 10 min, then a solution of N-phenyltrifluoromethane sulfonamide (19.5 g, 54.3 mmol) in 150 mL THF was added slowly. The reaction solution was warmed to r.t., poured onto saturated sodium bicarbonate, and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. The crude material was passed through silica (3% methanol, dichloromethane) to give the product as an oil.

Workup

  1. stirringThe solution was stirred for 10 min
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated sodium chloride
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-370d5aad46b6456da3ee4455b8759adf
Source dataset
uspto-grants-2001_07
Patent number
US06255315B1

Reaction notes

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