Tetrabutylammonium Fluoride → HCID 86641133, compound

HRID 2191065Notes

Reaction equation

HRID 2191065 reaction equation
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[CH:8]1[O:12][CH:11]([N:13]2[CH:18]=[CH:17][C:16](=[O:19])[NH:15][C:14]2=[O:20])[CH:10]([O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:20]=[C:14]1[NH:15][C:16](=[O:19])[CH:17]=[CH:18][N:13]1[CH:11]1[CH:10]([O:21][C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:9][CH:8]([CH2:7][OH:6])[O:12]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131730093HCID 131730093, compound

Product 1

HCID 86641133HCID 86641133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 50.2 (0.713 g, 1.06 mmol) was dissolved in 10 ml anhydrous THF was cooled to 0° C. Tetrabutyl ammonium fluoride (1.11 ml, 1N in THF, 1.11 mmol) was added dropwise and the reaction mixture was allowed to rise to room temperature. The reaction was stirred for 4 hr at room temperature while monitoring by TLC. When the reaction was complete by TLC the, solvent was removed under vacuum. The residue was re-dissolved in ethyl acetate (4 ml) and purified by column chromatography. Yield 0.300 g, 65.0%. Anal. 1H-NMR (CD3CN): δ 2.2 m 1H; 2.45 m 1H; 3.37 t 1H; 3.7 dd 1H; 3.97 dd 1H; 4.53 m 1H; 5.62 m 1H; 5.87 d 1H; 6.06 s 1H; 7.49-7.70 m 5H; 7.79 t 1H; 8.05 t 4H; 8.19 d 1H.

Workup

  1. customto rise to room temperature
  2. customwas removed under vacuum
  3. dissolutionThe residue was re-dissolved in ethyl acetate (4 ml)
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-506e7d4c68a54869bf2ee5d3c0b0bce7
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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