Dimethyl Sulfoxide → HCID 21883599, 화합물

HRID 722304노트

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HRID 722304 반응식
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[C:4]([CH:11]=[O:12])[CH:3]=1.CS(C)=O.[F:17][C:18]([F:27])([F:26])/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>C(OCC)C.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:10][CH:19]([C:18]([F:17])([F:27])[F:26])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]=2[CH:9]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 1229125-Chloro-2-hydroxyisophthalaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

생성물 1

HCID 21883599HCID 21883599, 화합물수율 35.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 21226206Ethyl acetate hexane용매

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온도
80 °C

실험 절차

A stirred solution of the dialdehyde (Step 2) (1.13 g, 6.14 mmol), dimethyl sulfoxide (6 mL), ethyl 4,4,4-trifluorocrotonate (1.37 mL, 1.55 g, 9.21 mmoL) and triethylamine (1.71 mL, 1.24 g, 12.28 mmol) in a round bottom flask fitted with condenser was heated to 80° C. for 8 h. Upon cooling to room temperature the reaction was diluted with diethyl ether (100 mL) and the resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL), dried over MgSO4, filtered and concentrated in vacuo yielding a tan powder. This powder was taken up in hot hexane-ethyl acetate and filtered to remove insoluble matter. Upon cooling of the filtrate, crystallization followed by vacuum filtration yielded the desired ester as tan crystals (0.726 g, 35%): mp 118.1–119.7° C. This material was of suitable purity to use without further purification.

후처리

  1. temperatureUpon cooling to room temperature the reaction
  2. washthe resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding a tan powder
  7. filtrationfiltered
  8. customto remove insoluble matter
  9. temperatureUpon cooling of the filtrate, crystallization
  10. filtrationfollowed by vacuum filtration

출처 및 근거

ORD 기록
ord-b83320cb706b45c3823c139ca43ab160
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138411B2

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