1-Penten-3-one → 2-(2-Hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone

HRID 859246

Reaction equation

HRID 859246 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15].[CH:16]([C:18]([CH2:20][CH3:21])=[O:19])=[CH2:17].C[O-].[Na+]>CO.CCOC(C)=O>[OH:1][CH2:2][CH2:3][C:4]1([CH2:17][CH2:16][C:18](=[O:19])[CH2:20][CH3:21])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15]

Participants

6

Reactant 3

HCID 153941-Penten-3-oneHCID 10942334Sodium MethoxideHCID 219908562-(2-Hydroxyethyl)-5-methoxy-1-indanone

Product 1

HCID 219909372-(2-Hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(2-hydroxyethyl)-5-methoxy-1-indanone (105 mg, 0.51 mmol) in methanol (2.0 mL) at room temperature was treated with ethyl vinyl ketone (EVK, 0.102 mL) and 0.5M sodium methoxide in methanol (0.204 mL, 0.1 mmol). The mixture was stirred in a capped flask and heated in an oil bath at 60° C. for 8 hours. After cooling, the reaction mixture was diluted with EtOAc (25 mL), washed with 0.2N HCl (15 mL), water (15 mL), and brine (15 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford 2-(2-hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone as an oil.

Workup

  1. temperatureAfter cooling
  2. washwashed with 0.2N HCl (15 mL), water (15 mL), and brine (15 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-4b7ff687c58e4abdb4ab1a6983d39969
Source dataset
uspto-grants-2006_12
Patent number
US07151196B2

Linked notes

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