Tetrabutylammonium Fluoride → HCID 89825024, compound

HRID 2273853Notes

Reaction equation

HRID 2273853 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:24]1([N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89824982HCID 89824982, compound

Product 1

HCID 89825024HCID 89825024, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(6-((tert-butyldimethylsilyl)oxy) hexyl)-N-cyclohexylbenzamide (242 mg, 0.58 mmol) was dissolved in THF (2 mL) and treated with TBAF (1M in THF, 0.72 mL, 0.72 mmol). The mixture was stirred at room temperature for overnight. The mixture was then concentrated and purified on silica gel with ethyl acetate:hexanes from 2:8 to 1:1 gave the desired product as a clear oil (136 mg, 77%). 1H NMR (300 MHz, CDCl3): δ 7.42-7.29 (m, 5H), 3.75-2.98 (m, 5H), 1.98-0.80 (m, 19H).

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-d260917a43464956bc694aa660a08343
Source dataset
uspto-grants-2015_09
Patent number
US09126937B2

Reaction notes

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