Tetrahydrofuran → HCID 136047814, compound

HRID 522571Notes

Reaction equation

HRID 522571 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH2:17][C@@H:18]([C:20]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)=[O:21])[N:19]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[S:16][CH:17]=[C:18]([C:20]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)=[O:21])[N:19]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 53363873HCID 53363873, compound

Product 1

HCID 136047814HCID 136047814, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a solution of 58a (0.2 mmol) in 5 mL CH2Cl2 was added a solution of tetrabutylammonium fluoride in THF (1 N, 0.6 mmol) and stirred at RT for around 14 h until reaction was finished by TLC monitor. 67.0% yield. 1H NMR (500 MHz, DMSO-d6) δ 10.1 (s, 1H), 8.51 (s, 1H), 7.85 (d, 2H, J=8.50 Hz), 7.62 (s, 2H), 6.91 (d, 2H, J=8.5 Hz), 3.86 (s, 6H), 3.79 (s, 3H). MS (ESI) m/z 394.1 (M+Na)+, 369.9 (M−H)−.

Sources & evidence

ORD record
ord-61c3abffa96641f398a63c747c87b569
Source dataset
uspto-grants-2016_05
Patent number
US09334242B2

Reaction notes

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