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

HRID 855993ノート

反応式

HRID 855993 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e0d9570265fa4b15a7bd50bb9b2f9895
出典データセット
uspto-grants-2007_08
特許番号
US07262318B2

反応ノート

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