Trimethylsilyl triflate → Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 706946Notes

Reaction equation

HRID 706946 reaction equation
C[Si](OS(C(F)(F)F)(=O)=O)(C)C.C[Si](C)(C)[O:15][CH2:16][CH2:17][O:18][Si](C)(C)C.O=[C:26]1[CH2:31][CH2:30][CH2:29][CH:28]([C:32]([O:34][CH3:35])=[O:33])[CH2:27]1>ClCCl>[O:15]1[C:26]2([CH2:31][CH2:30][CH2:29][CH:28]([C:32]([O:34][CH3:35])=[O:33])[CH2:27]2)[O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 566099Methyl 3-oxocyclohexane-1-carboxylate

Product 1

HCID 372311Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of trimethylsilyltrifluoromethanesulfonate (0.034 mL) in dry dichloromethane (5 mL) was added 1,2-bis(trimethylsiloxy)ethane (4.55 mL) followed by methyl 3-oxocyclohexanecarboxylate (2.9 g). The reaction mixture was stirred for 3 hours at −78° C. The reaction mixture was quenched with dry pyridine (0.5 mL), poured into saturated aqueous NaHCO3, and extracted with ether. The ether layer was dried over Na2CO3/Na2SO4. The reaction mixture was concentrated and purified by flash chromatography on silica with 5 to 30% ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe reaction mixture was quenched with dry pyridine (0.5 mL)
  2. additionpoured into saturated aqueous NaHCO3
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried over Na2CO3/Na2SO4
  5. concentrationThe reaction mixture was concentrated
  6. custompurified by flash chromatography on silica with 5 to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ccab818e9a8847958280b228c5ec5b04
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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