Water → HCID 69054367, compound

HRID 2103018Notes

Reaction equation

HRID 2103018 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[C:7]([C:13](=[O:15])[CH3:14])[C:6]=1[CH3:16])(=[O:3])[CH3:2].[C:17]1(=O)[CH2:20][CH2:19][CH2:18]1.N1[CH2:26][CH2:25][CH2:24][CH2:23]1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]([CH3:16])=[C:7]2[C:8](=[CH:9][C:10]=1[CH3:11])[O:12][C:17]1([CH2:20][CH2:19][CH2:18]1)[CH2:14][C:13]2=[O:15])(=[O:3])[CH3:2].[OH:4][C:5]1[C:6]([CH3:16])=[C:7]2[C:8](=[CH:9][C:10]=1[CH3:11])[O:12][C:23]1([CH2:26][CH2:25][CH2:24]1)[CH2:14][C:13]2=[O:15]

Participants

8

Reactant 4

HCID 962WaterHCID 14496CyclobutanoneHCID 31268PyrrolidineHCID 10220114HCID 10220114, compound

Product 2

HCID 69054367HCID 69054367, compoundHCID 69055157HCID 69055157, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 3-acetyl-4-hydroxy-2,6-dimethylphenyl acetate (13 g) and cyclobutanone (4.5 g) in toluene (150 mL) was added pyrrolidine (5.4 mL, 4.6 g). The solution was stirred at room temperature for 15 min and then refluxed for 5 hours equipped with Dean-Stark water trap. The solution was diluted with ethyl acetate, washed with diluted hydrochloride acid water solution, water and brine. Evaporation and chromatography (silica gel, hexane-ethyl acetate 1% to 10%) gave 5.5 g of 5,7-dimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate and 3.2 g of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one.

Workup

  1. temperaturerefluxed for 5 hours
  2. washwashed with diluted hydrochloride acid water solution, water and brine
  3. customEvaporation and chromatography (silica gel, hexane-ethyl acetate 1% to 10%)

Sources & evidence

ORD record
ord-01abf748ec4749b7a04148fe96039ee9
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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