Water → HCID 69056802, compound

HRID 2103043Notes

Reaction equation

HRID 2103043 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[CH3:17])(=O)C.[C:18]1(=O)[CH2:21][CH2:20][CH2:19]1.N1CCCC1.O>C1(C)C=CC=CC=1>[CH2:11]([C:10]1[CH:9]=[C:8]2[C:7]([C:14](=[O:16])[CH2:15][C:18]3([O:13]2)[CH2:21][CH2:20][CH2:19]3)=[C:6]([CH3:17])[C:5]=1[OH:4])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14496CyclobutanoneHCID 31268PyrrolidineHCID 86605489HCID 86605489, compound

Product 1

HCID 69056802HCID 69056802, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-acetyl-6-ethyl4-hydroxy-2-methylphenyl acetate (5.18 g), cyclobutanone (4.5 g) and pyrrolidine (1.5 mL) in toluene (50 mL) was stirred at refluxing temperature with a Dean Stark. After 8 hours it was poured into water and the toluene was separated, dried, and evaporated. The residue was dissolved in MeOH (50 mL) with LiOH (2 g), stirred at room temperature for 3 hours, poured into water, and extracted with ethyl acetate. The ethyl acetate was washed, dried, and evaporated. The residue was purified by silica gel column eluting with 15% ethyl acetate in hexane, giving 7-ethyl-6-hydroxy-5-methylspiro[chroman-2,1′-cyclobutan]-4-one as a light brown oil (0.82 g).

Workup

  1. temperatureat refluxing temperature with a Dean Stark
  2. customthe toluene was separated
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in MeOH (50 mL) with LiOH (2 g)
  6. stirringstirred at room temperature for 3 hours
  7. additionpoured into water
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate was washed
  10. customdried
  11. customevaporated
  12. customThe residue was purified by silica gel column
  13. washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-369391a7ad5b4bb4960220344e969db8
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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