Cyclobutanone → HCID 69055903, compound

HRID 2103035Notes

Reaction equation

HRID 2103035 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([OH:13])=[C:7]([C:14](=[O:16])[CH3:15])[C:6]=1[CH2:17][CH3:18])(=[O:3])[CH3:2].[C:19]1(=O)[CH2:22][CH2:21][CH2:20]1.N1CCCC1>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([CH2:17][CH3:18])=[C:7]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[O:13][C:19]1([CH2:22][CH2:21][CH2:20]1)[CH2:15][C:14]2=[O:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 31268PyrrolidineHCID 86605485HCID 86605485, compound

Product 1

HCID 69055903HCID 69055903, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-acetyl-2-ethyl-4-hydroxy-5,6-dimethylphenyl acetate (3.5 g) in 20 mL of toluene was added cyclobutanone (1.16 mL) and pyrrolidine (1.4 mL). The reaction was allowed to reflux for 2 hours and Dean-Stark apparatus was used to remove water from the reaction. After the reaction was complete, the mixture was extracted with ethyl acetate and then was washed with 1N HCl and water. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to give 5-ethyl-7,8-dimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate, which was hydrolyzed in 1N NaOH in MeOH/water. After the reaction was complete as indicated by TLC, the mixture was acidified with 1N HCl and extracted with ethyl acetate and dried over anhydrous Na2SO4. Evaporation of the solvents gave 0.8 g of 5-ethyl-6-hydroxy-7,8-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one as a yellow paste.

Workup

  1. temperatureto reflux for 2 hours
  2. customto remove water
  3. customfrom the reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwas washed with 1N HCl and water
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c56665e76e44a6e90bcaf633109cfba
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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