Acetonitrile → Diethyl P-2-naphthalenylphosphonate

HRID 1498989Notes

Reaction equation

HRID 1498989 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[Si](C)(C)C)(=O)=O.[F-].[Cs+].[P:25]([O-:28])([O-:27])[O-:26].[C:29](#N)[CH3:30].[CH3:32][CH2:33]OC(C)=O>>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[P:25](=[O:28])([O:27][CH2:29][CH3:30])[O:26][CH2:32][CH3:33]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 107908PhosphiteHCID 110785651-(Trimethylsilyl)naphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 13788025Diethyl P-2-naphthalenylphosphonate

Procedure

1-(trimethylsilyl)naphthalen-2-yl trifluoromethanesulfonate (25 mg, 0.073 mmol), Cesium Fluoride (60 mg, 0.395 mmol), Triethtyl phosphite (47 mg, 0.287 mmol), Acetonitrile (1 ml): Reaction Time 24 h; Rf: 0.3 (1:3 EtOAc:Pet. Ether); Thick oil; 15.5 mg, 82%; 1H NMR (400 MHz, CDCl3, TMS) δ 8.44 (d, J=15.6 Hz, 1H), 7.97-7.85 (m, 3H), 7.81-7.72 (m, 1H), 7.64-7.52 (m, 2H), 4.26-4.05 (m, 4H), 1.34 (t, J=7.0 Hz, 6H); 13C NMR (100 MHz, CDCl3, TMS) δ 135.0 (d, J=2.3 Hz), 134.0 (d, J=10.0 Hz), 132.3 (d, J=16.2 Hz), 128.9, 128.3 (d, J=14.7 Hz), 128.2, 127.8, 126.8, 126.4 (d, J=9.2 Hz), 125.3 (d, J=188.1 Hz), 62.1 (d, J=5.4 Hz), 16.3 (d, J=6.2 Hz); 31P NMR (162 MHz, CDCl3) δ 19.1; Mass (M+Na)+ 287; Known compound, Lit. M. Kalek, A. Ziadi, J. Stawinski, Org. Lett. 2008, 10, 4637.

Sources & evidence

ORD record
ord-27e02003d72746fcbdc431773b8d5429
Source dataset
uspto-grants-2015_12
Patent number
US09200018B2

Reaction notes

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