Ethanol → HCID 68753467, compound

HRID 333316Notes

Reaction equation

HRID 333316 reaction equation
[C:1]1(=[O:11])[C:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3](=[O:10])[O:2]1.[CH3:12][CH2:13][OH:14]>>[CH2:13]([O:14][C:3](=[O:10])[CH2:4][C:5]1([C:1]([OH:11])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:12]

Participants

3

Reactant 2

HCID 702EthanolHCID 27371022-oxaspiro[4.4]nonane-1,3-dione

Product 1

HCID 68753467HCID 68753467, compound

Conditions

Temperature
70 °C

Procedure

A solution of 2-oxaspiro[4.4]nonane-1,3-dione (522 mg, 3.39 mmol) in anhydrous EtOH (15 ml) was allowed to stir at 70° C. for 22 hours under nitrogen. The reaction mixture was concentrated to give a crude 1-(2-ethoxy-2-oxoethyl)cyclopentanecarboxylic acid (compound A, 672 mg). The product (86% purity) was used for next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 1.24 (t, J=7.2 Hz, 3H) 1.57-1.81 (m, 6H) 2.19-2.25 (m, 2H) 2.69 (s, 2H) 4.12 (q, J=7.2 Hz, 3H) 11.65 (br s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-eac45998f3804510bbb335e5fe226a3e
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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