Potassium Carbonate → HCID 22324896, compound

HRID 496423Notes

Reaction equation

HRID 496423 reaction equation
[OH:1][C:2]1[C:3]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Br[C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(#N)C>[CH3:34][C:28]([O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([CH3:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 22324784HCID 22324784, compound

Product 1

HCID 22324896HCID 22324896, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-hydroxy-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone (2.00 g, 7.5 mmol), potassium carbonate (2.08 g, 15.0 mmol), and acetonitrile (15 mL) was heated to reflux, whereupon ethyl 2-bromo-2-methylpropanoate (1.2 mL, 8.3 mmol) was added. The mixture was stirred at reflux for 2.5 h, whereupon further potassium carbonate (1.04 g, 7.5 mmol) and ethyl 2-bromo-2-methylpropanoate (1.2 mL, 8.3 mmol) were added. The mixture was stirred at reflux for a further 22 h and was then filtered and concentrated. The residue was purified by dry-flash column chromatography (SiO2, 5-30% ethyl acetate-hexane) to give ethyl 2-methyl-2-{[5-oxo-1-(2-phenylethyl)-5,6,7,8-tetrahydro-2-naphthalenyl]oxy}propanoate as a pale yellow oil, 2.75 g, 96% yield. NMR spectrum was consistent with structure. MS EI: M+• 380.1985 (M+• 380.1988). 2. 6-(2-Hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-1,2,3,4-tetrahydro-1-naphthalenol

Workup

  1. temperaturewas heated
  2. additionwas added
  3. additionwere added
  4. stirringThe mixture was stirred
  5. temperatureat reflux for a further 22 h
  6. filtrationwas then filtered
  7. concentrationconcentrated
  8. customThe residue was purified by dry-flash column chromatography (SiO2, 5-30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-12cbf64f6346469a83b72741f6c037c1
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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