Cyclobutanone → HCID 69055283, compound

HRID 2103015Notes

Reaction equation

HRID 2103015 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[CH3:17])(=[O:3])[CH3:2].[C:18]1(=O)[CH2:21][CH2:20][CH2:19]1>N1CCCCC1.C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]([CH3:17])=[C:7]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[O:13][C:18]1([CH2:21][CH2:20][CH2:19]1)[CH2:15][C:14]2=[O:16])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14496CyclobutanoneHCID 9859505HCID 9859505, compound

Product 1

HCID 69055283HCID 69055283, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A solution of the crude 3-acetyl-4-hydroxy-2,5,6-trimethyl-phenyl acetate prepared as in Step 1 (1.0 g), cyclobutanone (415 mg) and piperidine (10 drops) in xylenes (2 mL) was heated at 180° C. for 5 min and then 230° C. for 20 min using a microwave. The solution was diluted with ethyl acetate, washed with water and brine, dried, evaporated, and chromatographed (silica gel, hexane-ethyl acetate 3% to 8%) to give 354 mg of 5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate.

Workup

  1. washwashed with water and brine
  2. customdried
  3. customevaporated
  4. customchromatographed (silica gel, hexane-ethyl acetate 3% to 8%)

Sources & evidence

ORD record
ord-fab5119f314d4b4f8dc79b77426a2092
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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