Tetrabutylammonium Fluoride → 2-(Azocan-1-yl)ethanol

HRID 2368907Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[N:11]1([CH2:10][CH2:9][OH:8])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 866828951-(2-((Tert-butyldimethylsilyl)oxy)ethyl)azocane

Product 1

HCID 2274062-(Azocan-1-yl)ethanolYield 37%

Procedure

A solution of 1-(2-((tert-butyldimethylsilyl)oxy)ethyl)azocane (9.13 g, 33.7 mmol) and TBAF (1M in THF, 36 mmol) was stirred at room temperature overnight. The mixture was concentrated and purified on a silica gel column (eluting with DCM/MeOH=30/1˜50/1) to afford 2-(azocan-1-yl)ethanol (1.96 g, 37%). 1H NMR (DMSO-d6): δ 4.33 (br s, 1H), 3.45 (t, 2H), 2.53 (m, 6H), 1.54 (m, 10H); LCMS: 158 (M+H)+.

Workup

concentrationThe mixture was concentrated
custompurified on a silica gel column (eluting with DCM/MeOH=30/1˜50/1)

Sources & evidence

ORD record: ord-81e7f4e3e8f94e6fb8150f56d0df1fe4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703810B2

Reaction notes

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