Triphenylphosphine → N-Methyl-N-(1-phenylbut-3-enyl)benzenesulfonamide

HRID 860163

반응식

HRID 860163 반응식
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]1([CH:21](O)[CH2:22][CH:23]=[CH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:45][NH:46][S:47]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=[O:49])=[O:48]>C1COCC1.CCOCC.O>[CH3:45][N:46]([CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:22][CH:23]=[CH2:24])[S:47]([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)(=[O:48])=[O:49]

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 78858N-MethylbenzenesulfonamideHCID 2201191-Phenylbut-3-en-1-olHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 69447982N-Methyl-N-(1-phenylbut-3-enyl)benzenesulfonamide수율 79.3%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

DIAD (9.0 mL, 45.9 mmol) was added dropwise over 10 min to a stirred solution of 1-phenyl-3-buten-1-ol (4.0 g, 27.0 mmol), PPh3 (10.6 g, 40.5 mmol) and N-methylphenylsulfonamide (6.0 g, 35.0 mmol) in THF (200 mL) under N2 and the resulting mixture was stirred at RT for 20 h. H2O (200 mL) and Et2O (200 mL) were added and separated. The organics were washed with brine (150 mL) and concentrated under reduced pressure while loading on to MgSO4. The mixture was then purified by column chromatography on silica eluting with 3% Et2O/iso-hexanes to yield the sulfonamide (6.45 g, 79%). 1H NMR (CDCl3, 360 MHz) δ 7.78 (2H, d, J=7.8 Hz), 7.53 (1H, t, J=7.8 Hz), 7.44 (2H, t, J=7.8 Hz), 7.30–7.18 (5H, m), 5.67–5.52 (1H, m), 5.20 (1H, t, J=7.8 Hz), 5.02 (1H, dd, J=17.1, 1.5 Hz), 4.93 (1H, dd, J=10.2, 1.3 Hz), 2.70 (1H, app. quintet, J=7.1 Hz), 2.65 (3H, s), 2.44 (1H, app. quintet, J=7.1 Hz).

후처리

  1. customseparated
  2. washThe organics were washed with brine (150 mL)
  3. concentrationconcentrated under reduced pressure while loading on to MgSO4
  4. customThe mixture was then purified by column chromatography on silica eluting with 3% Et2O/iso-hexanes

출처 및 근거

ORD 기록
ord-6349e2eb4bec40f69ec546faccdeb9ad
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153868B2

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