Triphenylphosphine → 4-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene

HRID 855993노트

반응식

HRID 855993 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[CH3:11][C:12]1[CH:19]=[C:18]([CH:17]=[C:14]([CH3:15])[CH:13]=1)[CH2:20][S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 158094-NitrobenzenethiolHCID 337063,5-Dimethylbenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 694205454-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene수율 50%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-nitrothiophenol (0.400 g, 2.57 mmol), 3,5-dimethylbenzyl alcohol (0.38 ml, 2.57 mmol) and triphenylphosphine (0.743 g, 2.84 mmol) in 10 ml anhydrous tetrahydrofuran was added diethyl azodicarboxylate (0.446 ml, 2.84 mmol). The reaction mixture was stirred overnight at room temperature under nitrogen. It was then diluted with 90 ml ethyl acetate and the resulting solution was washed sequentially with 70 ml saturated aqueous sodium bicarbonate solution, 70 ml water and 70 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The solid residue was triturated with 95:5 hexane/ethyl acetate (20 ml) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel, 15 g), eluting with 95:5 hexane/ethyl acetate to yield title compound as a yellow solid (0.35 g, 50% yield). 1H NMR (400 MHz, CD3Cl): δ2.30 (s, 6H), 4.18 (s, 2H), 6.92 (s, 1H), 7.0 (s, 2H), 7.33 (d, 2H), 8.10 (d, 2H).

후처리

  1. washthe resulting solution was washed sequentially with 70 ml saturated aqueous sodium bicarbonate solution, 70 ml water and 70 ml brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe solid residue was triturated with 95:5 hexane/ethyl acetate (20 ml)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, 15 g)
  8. washeluting with 95:5 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-e0d9570265fa4b15a7bd50bb9b2f9895
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262318B2

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