Sodium Carbonate → HCID 59226595, 화합물

HRID 73574

반응식

HRID 73574 반응식
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].[O:16](S(C(F)(F)F)(=O)=O)[S:17]([C:20]([F:23])([F:22])[F:21])(=O)=[O:18]>C(Cl)Cl>[F:21][C:20]([F:23])([F:22])[S:17]([O:8][C:6]1[CH2:7][CH:2]([CH3:1])[CH2:3][C:4](=[O:9])[CH:5]=1)(=[O:18])=[O:16]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 67749Trifluoromethanesulfonic anhydrideHCID 4580955-Methylcyclohexane-1,3-dione

생성물 1

HCID 59226595HCID 59226595, 화합물수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 5-methylcyclohexane-1,3-dione (1 equiv) in DCM (0.4M) was added Na2CO3 (1.0 equiv.) and cooled to 0° C. Added Tf2O (1.0 equiv.) in DCM (5M) dropwise over 1 hr at 0° C. under a nitrogen atmosphere. Upon addition, the reaction was stirred for 2 hr at room temperature (dark red solution). The solution was filtered and to the filtrate was added saturated NaHCO3 (carefully), then extracted the organics, dried with brine, then Na2SO4, and concentrated. The crude was purified via SiO2 column chromatography eluting with DCM and hexanes (1:1) or alternatively via a neutral alumina plug eluting with DCM to afford 5-methyl-3-oxocyclohex-1-enyl trifluoromethanesulfonate in 30% or 67% yield respectively. The triflate decomposes upon storage and should be used immediately for the next reaction. LC/MS=259.1/300.1 (M+H and M+CH3CN); Rt=0.94 min, LC=3.84 min.

후처리

  1. additionUpon addition
  2. filtrationThe solution was filtered and to the filtrate
  3. additionwas added saturated NaHCO3 (carefully),
  4. extractionthen extracted the organics,
  5. dry with materialdried with brine
  6. concentrationNa2SO4, and concentrated
  7. customThe crude was purified via SiO2 column chromatography
  8. washeluting with DCM and hexanes (1:1) or alternatively via a neutral alumina plug
  9. washeluting with DCM

출처 및 근거

ORD 기록
ord-89a405d6876d4493a9b558a4765ec075
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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