Cyclobutanone → HCID 69053186, compound

HRID 2103047Notes

Reaction equation

HRID 2103047 reaction equation
C([O:4][C:5]1[C:10]([CH2:11][CH3:12])=[CH:9][C:8]([OH:13])=[C:7]([C:14](=[O:16])[CH3:15])[C:6]=1[CH2:17][CH3:18])(=O)C.[C:19]1(=O)[CH2:22][CH2:21][CH2:20]1.N1CCCC1>C1(C)C=CC=CC=1>[CH2:17]([C:6]1[C:5]([OH:4])=[C:10]([CH2:11][CH3:12])[CH:9]=[C:8]2[C:7]=1[C:14](=[O:16])[CH2:15][C:19]1([O:13]2)[CH2:22][CH2:21][CH2:20]1)[CH3:18]

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 31268PyrrolidineHCID 86605491HCID 86605491, compound

Product 1

HCID 69053186HCID 69053186, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-acetyl-2,6-diethyl-4-hydroxyphenyl acetate (4.0 g) and cyclobutanone (1.23 g) in toluene (150 mL) was added pyrrolidine (568 mg). 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. After evaporation, the residue was dissolved in methanol and a lithium hydroxide solution (10%) was added until the solution reached a pH value greater than 9. The solution was stirred at room temperature for 2 hours and then neutralized to pH 7 using diluted hydrochloric acid. Work up and chromatography (silica gel, hexane-ethyl acetate 2% to 8%) gave 1.8 g of 5,7-diethyl-6-hydroxyspiro[chroman-2,1′-cyclobutan]-4-one. 1H-NMR (300 MHz, CDCl3) δ=6.67 (s, 1H), 5.14 (s, 1H), 4.01 (s, 3H), 3.11 (q, J=7.4 Hz, 2H), 2.84 (s, 2H), 2.65 (q, J=7.4 Hz, 2H), 2.30-1.65 (m, 6H), 1.30-1.10 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=194.3, 155.0, 146.0, 139.9, 130.6, 117.0, 115.8, 79.8, 47.7, 33.0, 23.8, 19.8, 13.9, 13.2, 12.1 ppm.

Workup

  1. temperaturerefluxed for two hours
  2. customto remove the water
  3. customAfter evaporation
  4. dissolutionthe residue was dissolved in methanol
  5. additiona lithium hydroxide solution (10%) was added until the solution

Sources & evidence

ORD record
ord-3276376220c54719969a39d4e3629b31
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…