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

HRID 574854

반응식

HRID 574854 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87ecc851e4b04689aa57159a870aec57
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034875B2

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