Acetonitrile → HCID 5106509, compound

HRID 1498985Notes

Reaction equation

HRID 1498985 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][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][O:13][C:9]1[CH:8]=[C:7]([P:23](=[O:26])([O:25][CH2:27][CH3:28])[O:24][CH2:30][CH3:31])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 107908PhosphiteHCID 110239333-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate

Product 1

HCID 5106509HCID 5106509, compound

Procedure

3-methoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.076 mmol), Cesium Fluoride (63 mg, 0.419 mmol), Triethtyl phosphite (50 mg, 0.304 mmol), Acetonitrile (1 ml): Reaction Time: 24 h; Rf: 0.3 (2:3 EtOAc:Pet Ether); Thick oil; 13.7 mg, 74%; 1H NMR (200 MHz, CDCl3, TMS) δ 7.45-7.28 (m, 3H), 7.15-7.01 (m, 1H), 4.25-3.96 (m, 4H), 3.85 (s, 3H), 1.33 (t, J=7.1 Hz, 6H); 13C NMR (100 MHz, CDCl3, TMS) δ 159.4 (d, J=18.5 Hz), 129.7 (d, J=17.7 Hz), 129.6 (d, J=187.3 Hz), 124.0 (d, J=9.3 Hz), 118.8 (d, J=3.1 Hz), 116.4 (d, J=11.6 Hz), 62.2 (d, J=5.4 Hz), 55.41, 16.3 (d, J=6.2 Hz); 31P NMR (162 MHz, CDCl3) δ 18.7; Mass (M+Na)+ 267; Known Compound, Lit. G. Yang, C. Shen, L. Zhang, W. Zhang. Tetrahedron Lett. 2011, 52, 5032.

Workup

  1. custom24 h

Sources & evidence

ORD record
ord-808402ce51fe465c950623c180b34fdf
Source dataset
uspto-grants-2015_12
Patent number
US09200018B2

Reaction notes

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