Sodium Carbonate → HCID 59226595、化合物

HRID 73574

反応式

HRID 73574 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 59226595HCID 59226595、化合物収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-89a405d6876d4493a9b558a4765ec075
出典データセット
uspto-grants-2014_09
特許番号
US08829193B2

関連ノート

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