Ethanol → 2-(Pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one

HRID 1776376Notes

Reaction equation

HRID 1776376 reaction equation
O[C:2]1([C:7]#[C:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(NCC)C.C([OH:24])C>>[N:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:2]3([CH2:6][CH2:5][CH2:4][CH2:3]3)[C:7](=[O:24])[CH:8]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 8021DiethylamineHCID 59354791HCID 59354791, compound

Product 1

HCID 593547772-(Pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one

Procedure

To a stirred solution of 3-(1-hydroxycyclopentyl)-1-(pyridin-4-yl)prop-2-yn-1-one (0.42 g, 1.95 mmol) in ethanol (10 mL) was added diethyl amine (0.21 g, 2.9 mmol) EtOH (1 mL) dropwise at RT and the reaction mixture was stirred for additional 1 h. Then the EtOH was removed, diluted with EtOAc (20 mL), washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford 2-(pyridin-4-yl)-1-oxaspiro[4.4]non-2-en-4-one (0.4 g) as an oil.

Workup

  1. customThen the EtOH was removed
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed with water (10 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb42669ed9bb44a9b2bf66c688100d26
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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