Acetonitrile → HCID 11630100, compound

HRID 1498984Notes

Reaction equation

HRID 1498984 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+].[P:23]([O-:26])([O-:25])[O-:24].[C:27](#N)[CH3:28].[CH3:30][CH2:31]OC(C)=O>>[CH3:14][C:9]1[CH:10]=[CH:11][C:12]([CH3:13])=[CH:7][C:8]=1[P:23](=[O:26])([O:25][CH2:27][CH3:28])[O:24][CH2:30][CH3:31]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 107908PhosphiteHCID 90037234HCID 90037234, compound

Product 1

HCID 11630100HCID 11630100, compound

Procedure

3,6-dimethyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.076 mmol), Cesium Fluoride (64 mg, 0.421 mmol), Triethtyl phosphite (50 mg, 0.306 mmol), Acetonitrile (1 ml): Reaction Time: 35 h; Rf: 0.3 (1:4 EtOAc:Pet Ether); Thick oil; 16.1 mg, 87%; 1H NMR (400 MHz, CDCl3, TMS) δ 7.75 (d, J=14.8, 1 H), 7.23 (d, J=7.8 Hz, 1H), 7.17-7.10 (m, 1H), 4.21-4.00 (m, 4H), 2.52 (s, 3H), 2.34 (s, 3H), 1.33 (t, J=7.3 Hz, 6H); 13C NMR (100 MHz, CDCl3, TMS) δ 138.5 (d, J=10.0 Hz), 134.9 (d, J=14.6 Hz), 134.5 (d, J=10.8 Hz), 133.2, 131.1 (d, J=15.4 Hz), 126.3 (d, J=182.7 Hz), 61.8 (d, J=5.4 Hz), 20.7, 20.6, 16.3 (d, J=6.2 Hz); 31P NMR (162 MHz, CDCl3) δ 20.0; Mass (M+Na)+ 265; Known Compound, Lit. S. Branion, V. Benin, Synth. Commun. 2006, 36, 2121.

Workup

  1. custom35 h

Sources & evidence

ORD record
ord-8c603549cc0a438ba68ff52cf889e313
Source dataset
uspto-grants-2015_12
Patent number
US09200018B2

Reaction notes

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