Dimethylformamide → Benzofuran-6-carbaldehyde

HRID 379259

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HRID 379259 반응식
[O:1]1[C:5]2[CH:6]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C1(P(CCC)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C([SiH](CCCCCCCC)CCCCCCCC)CCCCCCC.CN([CH:69]=[O:70])C>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:1]1[C:5]2[CH:6]=[C:7]([CH:69]=[O:70])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

참가 물질

8

반응물 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 82100DiphenylpropylphosphineHCID 87780Trioctylsilane, 95%HCID 11357589Benzofuran-6-YL trifluoromethanesulfonate

생성물 1

HCID 14354086Benzofuran-6-carbaldehyde

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A solution of triflate 20-3 (0.798 g, 3.0 mmol), Pd(OAc)2 (13.5 mg, 0.060 mmol), and diphenylphosphinopropane (24 mg, 0.060 mmol) in DMF (15 mL) was heated to 70° C. with a gentle flow of CO (g) passing through it. Triethylamine (1.66 mL, 12 mmol) was added followed by trioctylsilane (2.70 mL, 6.0 mmol). The solution was maintained at 70° C. for 2 h, and cooled to room temperature. The solution was diluted with water (10 mL). The mixture was extracted with Et2O (2×30 mL). The combined organic extracts were washed with brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (5% acetone/hexanes) to give the desired aldehyde 20-4.

후처리

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with Et2O (2×30 mL)
  3. washThe combined organic extracts were washed with brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (5% acetone/hexanes)

출처 및 근거

ORD 기록
ord-4dec237814344d38a9895d143573b57b
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297249B1

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