Triethylamine → 1,4-Dioxaspiro[4.4]non-7-ene

HRID 1750554Notes

Reaction equation

HRID 1750554 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C[Si](C)([O:16][CH2:17][CH2:18][O:19][Si](C)(C)C)C.[C:25]1(=O)[CH2:29][CH:28]=[CH:27][CH2:26]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:16]1[C:28]2([CH2:27][CH:26]=[CH:25][CH2:29]2)[O:19][CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 84351Cyclopent-3-en-1-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 130147471,4-Dioxaspiro[4.4]non-7-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of trimethylsilyl trifluoromethanesulfonate (CAS number 27607-77-8; 0.22 ml, 1.22 mmol) in DCM (12 ml) at −78° C. was successively added 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (CAS number 7381-30-8; 2.51 g, 12.18 mmol) and cyclopent-3-en-1-one (CAS number 14320-37-7; 1 g, 12.18 mmol). The reaction mixture was stirred at −78° C. for 3 hours, quenched with triethylamine (2 ml, 14.35 mmol), poured into a saturated solution of sodium bicarbonate and extracted with diethyl ether. The organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. customat −78° C.
  2. extractionextracted with diethyl ether
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a922cc938dc1493f861289b8d5c3db2f
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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