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

HRID 1815047Notes

Reaction equation

HRID 1815047 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 5d 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-168e60ebf5404699916e1ea3575dd1c6
Source dataset
uspto-grants-2005_04
Patent number
US06878718B2

Reaction notes

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