Cyclobutanone → HCID 69053183, compound

HRID 2103049Notes

Reaction equation

HRID 2103049 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([OH:14])=[C:7]([C:15](=[O:17])[CH3:16])[C:6]=1[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]([CH3:18])=[C:7]2[C:8](=[CH:9][C:10]=1[CH:11]([CH3:13])[CH3:12])[O:14][C:19]1([CH2:22][CH2:21][CH2:20]1)[CH2:16][C:15]2=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 31268PyrrolidineHCID 86605493HCID 86605493, compound

Product 1

HCID 69053183HCID 69053183, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-acetyl-4-hydroxy-6-isopropyl-2-methylphenyl acetate (8.5 g) and cyclobutanone (2.6 g) in toluene (150 mL) was added pyrrolidine (1.2 g). The solution was left at room temperature for 16 hours, refluxed for two hours, and then a Dean-Stark was used to remove the water. Work up and chromatography (silica gel, hexane-ethyl acetate 2% to 5%) gave 4 g of 7-isopropyl-5-methyl-4-oxospiro[chroman-2,1′-cyclobutane]-6-yl acetate.

Workup

  1. temperaturerefluxed for two hours
  2. customto remove the water

Sources & evidence

ORD record
ord-406b9712a52e4382b8f7d1d5e657a8cc
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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