4-Hydroxy-1-indanone → HCID 67111152, compound

HRID 2363115Notes

Reaction equation

HRID 2363115 reaction equation
[CH3:1][C:2]([O-:5])(C)[CH3:3].[K+].O[C:8]1[CH:16]=[CH:15]C=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=O>CCOCC>[CH:10](=[C:9]1[C:8]2[CH:16]=[CH:15][CH:3]=[C:2]([OH:5])[C:1]=2[CH2:12][CH2:13]1)[CH3:11]

Participants

4

Reactant 2

HCID 5905474-Hydroxy-1-indanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67111152HCID 67111152, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of CH3CH2PPh3I (677 mg, 1.62 mmol) in Et2O (10 mL) was added t-BuOK (181 mg, 1.62 mmol). The mixture was stirred for 15 minutes, to which was added dropwise 4-hydroxy-indan-1-one (200 mg, 1.35 mmol). The mixture was stirred at room temperature overnight and then diluted with diethylether. The mixture was filtered on a pad of celite, and the filtrate was concentrated. The crude residue was purified by column chromatography to give 1-ethylidene-indan-4-ol (37 mg, 17%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationThe mixture was filtered on a pad of celite
  3. concentrationthe filtrate was concentrated
  4. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-84ffd0e65b794f49b55e3b44fbed8e79
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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