Tetrabutylammonium Fluoride → HCID 11964319, compound

HRID 1785567Notes

Reaction equation

HRID 1785567 reaction equation
[Si]([O:8][CH:9]1[CH2:18][C:17]2[C:16]([N:19]([CH3:35])[C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[CH:23][N:24]=3)=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:35][N:19]([C:20]1[O:21][C:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=2)=[CH:23][N:24]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH2:18][CH:9]([OH:8])[CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67229253HCID 67229253, compound

Product 1

HCID 11964319HCID 11964319, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 18E (56 mg, 0.112 mmol) in 6 mL of tetrahydrofuran was treated with a solution of tetrabutylammonium fluoride (1M-in-tetrahydrofuran, 1 mL, 1 mmol). The reaction mixture was stirred at rt for 4 h, then the solvent was evaporated, and the residue was chromatographed on silica gel, eluting with 70% ethyl acetate-hexane, to afford the title compound as a tan foam (27 mg, 62%). 1H NMR (DMSO-d6) δ 7.70 (d, J=8.4 Hz, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.57 (s, 1H), 7.11-7.22 (m, 3H), 4.78 (d, J=3.7 Hz, 1H), 3.86 (m, 1H), 3.38 (s, 3H), 2.73-2.98 (m, 3H), 2.37 (m, 1H), 1.89 (m, 1H), 1.63 (m, 1H); MS (ESI+) m/z 389 (M+H)+.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was chromatographed on silica gel
  3. washeluting with 70% ethyl acetate-hexane

Sources & evidence

ORD record
ord-72ae43375b92458aa55315b89e4ff103
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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