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

HRID 655473Notes

Reaction equation

HRID 655473 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 702Ethanol2×HCID 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) in 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-d02ce98f97c34b039d5a21753371d9ca
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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