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

HRID 860163

反応式

HRID 860163 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6349e2eb4bec40f69ec546faccdeb9ad
出典データセット
uspto-grants-2006_12
特許番号
US07153868B2

関連ノート

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