p-Toluenesulfinic acid → (E)-P,P-Diphenyl-N-(1-tosylhex-2-en-1-yl)phosphinic amide
Reaction equation
[C:1]1([P:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16](=O)/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21].[C:23]1([CH3:32])[CH:28]=[CH:27][C:26]([S:29]([OH:31])=[O:30])=[CH:25][CH:24]=1>>[C:1]1([P:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])[NH:8][CH:16]([S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:32])=[CH:24][CH:25]=2)(=[O:31])=[O:30])/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
The title compound is synthesized following a previously reported procedure7 from P,P-diphenylphosphinic amide (2.17 g, 10.0 mmol, 1.00 equiv.), (E)-hex-2-enal (2.31 mL, 20.0 mmol, 2.00 equiv.), and p-toluenesulfinic acid (2.34 g, 15.0 mmol, 1.50 equiv.) to obtain S5 as white solid (3.22 g, 7.10 mmol, 71% yield). M.p.=138-139° C. IR (neat): 3177 (w, br), 2959 (w), 2933 (w), 2870 (w), 1661 (m), 1596 (w), 1437 (m), 1300 (m), 1281 (m), 1214 (m), 1185 (s), 1170 (m), 1138 (m), 1125 (s), 1106 (m), 1083 (m), 955 (m), 894 (m), 752 (m), 726 (s), 693 (s), 662 (m), 583 (s), 568 (m), 536 (s) cm−1; 1H NMR (400 MHz, CDCl3): δ 7.79-7.71 (4H, m), 7.59 (2H, d, J=8.4 Hz), 7.59-7.54 (2H, m), 7.50-7.43 (4H, m), 7.23 (2H, d, J=8.0 Hz), 5.90 (1H, ddd, J=13.6, 11.6, 9.6 Hz), 5.31 (1H, t, J=10.0 Hz), 4.73 (1H, dd, J=14.0, 10.4 Hz), 3.28 (1H, app td, J=10.8, 3.6 Hz), 2.42 (3H, s), 1.97-1.88 (1H, m), 1.52-1.32 (2H, m), 1.20-1.10 (1H, m), 0.82 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3): δ 144.3, 134.7, 132.8, 132.6 (d, J=2.9 Hz), 132.5 (d, J=2.9 Hz), 132.2 (d, J=10.1 Hz), 131.9 (d, J=10.1 Hz), 131.4 (d, J=128.0 Hz), 131.1 (d, J=128.0 Hz), 129.6, 129.2, 128.9 (d, J=12.9 Hz), 128.9 (d, J=13.0 Hz), 101.9 (d, J=9.9 Hz), 67.6, 29.7, 21.8, 20.0, 13.7.
Sources & evidence
- ORD record
- ord-819a3df950a04881b8332ff8daac245c
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328061B2
Reaction notes
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