Acetonitrile → HCID 118260395, compound

HRID 1498990Notes

Reaction equation

HRID 1498990 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([CH3:14])[C:8]=1[Si](C)(C)C)(=O)=O.[F-].[Cs+].[C:23]1([P:29]([O:33]CC)[O:30][CH2:31][CH3:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(#N)C>CCOC(C)=O>[CH3:14][C:9]1[CH:10]=[CH:11][C:12]([CH3:13])=[CH:7][C:8]=1[P:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:33])[O:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 25953Cesium fluorideHCID 74225Diethyl phenylphosphoniteHCID 90037234HCID 90037234, compound

Product 1

HCID 118260395HCID 118260395, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3,6-dimethyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.077 mmol), Cesium Fluoride (64 mg, 0.421 mmol), Diethyl phenylphosphonite (60 mg, 0.306 mmol), Acetonitrile (1 ml): Reaction Time: 32 h; Rf: 0.4 (1:1 EtOAc:Pet Ether); Thick oil; 13.0 mg, 62%; 1H NMR (400 MHz, CDCl3, TMS) δ 7.81-7.70 (m, 3H), 7.52-7.40 (m, 3H), 7.23 (d, J=7.8 Hz, 1H), 7.12-7.05 (m, 1H), 4.11 (apparent quint, J=7.0 Hz, 2H), 2.36 (s, 3H), 2.33 (s, 3H), 1.38 (t, J=7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3, TMS) δ 138.6 (d, J=10.8 Hz), 135.0 (d, J=12.3 Hz), 133.9 (d, J=9.3 Hz), 132.5 (d, J=124.1 Hz), 128.4 (d, J=13.4 Hz), 131.7, 131.5 (d, J=7.7 Hz), 131.4, 131.3, 129.0 (d, J=133.3 Hz), 128.4 (d, J=13.1 Hz), 60.7 (d, J=5.4 Hz), 20.9, 20.7 (d, J=3.9 Hz), 16.4 (d, J=6.9 Hz); 31P NMR (162 MHz, CDCl3,) δ 32.2; HRMS-ESI (m/z) calcd (C16H19O2P+H)+: 275.1195. found: 275.1193.

Workup

  1. custom32 h

Sources & evidence

ORD record
ord-c093b41f22e6415886f2a03ef6bb63d1
Source dataset
uspto-grants-2015_12
Patent number
US09200018B2

Reaction notes

Loading…