Acetonitrile → HCID 23591704, compound

HRID 1498986Notes

Reaction equation

HRID 1498986 reaction equation
FC(F)(F)S(O[C:7]1[C:15]([Si](C)(C)C)=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1)(=O)=O.[F-].[Cs+].[P:24]([O-:27])([O-:26])[O-:25].[C:28](#N)[CH3:29].[CH3:31][CH2:32]OC(C)=O>>[O:13]1[C:9]2[CH:8]=[CH:7][C:15]([P:24](=[O:27])([O:26][CH2:28][CH3:29])[O:25][CH2:31][CH3:32])=[CH:14][C:10]=2[O:11][CH2:12]1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 107908PhosphiteHCID 11210047HCID 11210047, compound

Product 1

HCID 23591704HCID 23591704, compound

Procedure

6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl trifluoromethanesulfonate (25 mg, 0.073 mmol), Cesium Fluoride (61 mg, 0.402 mmol), Triethtyl phosphite (48 mg, 0.292 mmol), Acetonitrile (1 ml): Reaction Time: 16 h; Rf: 0.3 (2:3 EtOAc:Pet Ether); Thick oil; 16.0 mg, 85%; 1H NMR (500 MHz, CDCl3, TMS) δ 7.38 (dd, J=7.9, 14.0 Hz, 1H), 7.20 (d, J=12.8 Hz, 1H), 6.88 (dd, J=3.4, 7.6 Hz, 1H), 6.03 (s, 2H), 4.17-4.01 (m, 4H), 1.32 (t, J=7.0 Hz, 6H); 13C NMR (100 MHz, CDCl3, TMS) δ 151.2 (d, J=2.9 Hz), 147.8 (d, J=22.9 Hz), 127.4 (d, J=11.4 Hz), 121.3 (d, J=193.6 Hz), 111.2 (d, J=12.4 Hz), 108.6 (d, J=18.1 Hz), 101.5, 62.0 (d, J=5.7 Hz), 16.3 (d, J=6.7 Hz); 31P NMR (162 MHz, CDCl3) δ 19.0; Mass (M+Na)+ 281; Known Compound, Lit. G. Yang, C. Shen, L. Zhang, W. Zhang. Tetrahedron Lett. 2011, 52, 5032.

Workup

  1. custom16 h

Sources & evidence

ORD record
ord-79c998c2948047e69350f7b4e50cd6a2
Source dataset
uspto-grants-2015_12
Patent number
US09200018B2

Reaction notes

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