Propanal → 2-(2-Oxobutyl)-4-hydroxy-1-indanone

HRID 974781Notes

Reaction equation

HRID 974781 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:12](=[O:15])[CH2:13][CH3:14].C(N([CH2:21][CH3:22])CC)C.[CH2:23]([OH:25])[CH3:24]>[I-].C[N+]1C(C)=C(CCO)SC=1.C(Cl)Cl>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[CH2:12])[C:8]2=[O:11])=[CH:4][CH:3]=1.[O:15]=[C:12]([CH2:21][CH3:22])[CH2:13][CH:14]1[CH2:2][C:10]2[C:9](=[CH:5][CH:4]=[CH:24][C:23]=2[OH:25])[C:8]1=[O:11]

Participants

8

Reactant 4

HCID 527PropanalHCID 702EthanolHCID 8471TriethylamineHCID 70206596-Hydroxy-1-indanone

Product 2

HCID 199694252-(2-Oxobutyl)-4-hydroxy-1-indanoneYield 70%HCID 199694276-Hydroxy-2-methylene-1-indanone

Reagents, catalysts & solvents 2

HCID 98387703,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

6-Hydroxy-2-methylene-1-indanone was prepared using a similar method to that described in Example 16 but using 6-hydroxy-1-indanone instead of 4-hydroxy-1-indanone. To the above compound (0.3 g; 1.87 mmol) in suspension in ethanol, were added, at ambient temperature, under argon: propionaldehyde (0.27 ml; 3.75 mmol), triethylamine (80 μl; 0.56 mmol) and 3,4-dimethyl-5-(2hydroxyethyl)thiazolium iodide (50.6 mg; 0.18 mmol). The mixture was heated at 80° C. for 17 hours. The solution was taken up in CH2Cl2 and washed in water and a saturated solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (7/3), to give 2-(2-oxobutyl)-4-hydroxy-1-indanone (0.28 g; 70%).

Workup

  1. washwashed in water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with petroleum ether/ethyl acetate (7/3)

Sources & evidence

ORD record
ord-7cb3c88aa8c04ff1a59864567197c248
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

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