Triethylamine → 3-Ethoxyspiro[3.6]decan-1-one

HRID 491554Notes

Reaction equation

HRID 491554 reaction equation
[CH:1]1([C:8](Cl)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11]([O:13][C:14]#[CH:15])[CH3:12].C(N(CC)CC)C>C(OCC)C>[CH2:11]([O:13][CH:14]1[C:1]2([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8](=[O:9])[CH2:15]1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61239Ether, ethyl ethynylHCID 12556870Cycloheptanecarbonyl chloride

Product 1

HCID 219195623-Ethoxyspiro[3.6]decan-1-oneYield 87.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of cycloheptyl carbonyl chloride (10.0 g, 0.062 mol) and ethoxyacetylene (40% w/w solution in hexanes, 6.0 g, 0.083 mol, 12 ml) in diethylether (50 ml) was treated dropwise with triethylamine (20 ml, 0.14 mol) and the reaction stirred for 5 d at room temperature. Filtration and concentration of the filtrate in vacuo followed by chromatography (SiO2, 5:1 EtOAc:hexanes) gave the title compound as a pale yellow oil (10.5 g, 0.054 mol, 87%). δH (CDCl3, 300K) 4.78 (1H, s), 4.20 (2H, q J 7.1 Hz), 1.94-1.87 (2H, m), 1.83-1.77 (2H, m), 1.71-1.66 (2H, m), 1.63-1.52 (6H, m), 1.45 (3H, t J 7.1 Hz); m/z (ES+, 70V) 194.9 (MH+).

Workup

  1. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-7d1cc95f05d8427cbdd6820578c8267f
Source dataset
uspto-grants-2009_05
Patent number
US07531549B2

Reaction notes

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