Cesium carbonate → 3,3,4,4-Tetrafluoro-2,3,4,5-tetrahydro-1,6-benzodioxocine-8-carbaldehyde

HRID 2264149노트

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HRID 2264149 반응식
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(O[CH2:17][C:18]([F:32])([F:31])[C:19]([F:30])([F:29])[CH2:20][O:21]S(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:29][C:19]1([F:30])[CH2:20][O:21][C:9]2[CH:2]=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=2[O:10][CH2:17][C:18]1([F:32])[F:31]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 943653,5-DihydroxybenzaldehydeHCID 149438532,2,3,3-Tetrafluorobutane-1,4-diyl bis(trifluoromethanesulfonate)

생성물 1

HCID 602097233,3,4,4-Tetrafluoro-2,3,4,5-tetrahydro-1,6-benzodioxocine-8-carbaldehyde

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

A mixture of 2 g of 3,5-dihydroxybenzaldehyde, 10 g of 2,2,3,3-tetrafluorobutane-1,4-diyl bis(trifluoromethanesulfonate) and 12 g of cesium carbonate in 100 mL of anhydrous acetonitrile was heated under nitrogen to 50° C. overnight. The mixture was allowed to cool, then filtered and concentrated under reduced pressure. The residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate then dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-35% ethyl acetate in hexanes) gave the product as crystalline solid. MS (m+1)=265.1; 1H NMR (400 MHz, CDCl3) 9.85 (s, 1H), 7.6 (m, 2H), 7.2 (d, 1H), 4.64 (t, 2H), 4.45 (t, 2H).

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0-35% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-64d15b8f533048edae3baf750ff9c5ac
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855201B2

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