Water → Methyl 3-(3-oxo-6-pentyloxyindan-5-yloxymethyl)benzoate

HRID 242448Notes

Reaction equation

HRID 242448 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.I[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:19](=O)([O-])[O-].[Cs+].[Cs+].O.CC[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[C:33]([O:36][CH2:37]C)(=[O:35])[CH3:34]>CN(C=O)C>[O:12]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28])=[C:10]([O:11][CH2:18][C:17]3[CH:19]=[C:34]([CH:14]=[CH:15][CH:16]=3)[C:33]([O:36][CH3:37])=[O:35])[CH:9]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 962WaterHCID 10796Cesium carbonateHCID 123351-IodopentaneHCID 115934875,6-Dihydroxy-2,3-dihydro-1H-inden-1-oneHCID 21899848Ethylacetate heptane

Product 1

HCID 57458787Methyl 3-(3-oxo-6-pentyloxyindan-5-yloxymethyl)benzoateYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5,6-dihydroxyindanone (2.2 g; 13.4 mmol), iodopentane (1.75 ml; 13.4 mmol) and caesium carbonate (Cs2CO3; 4.8 g; 14.7 mmol) in DMF (50 ml) is heated at 40° C. for 35 minutes. The medium is cooled to room temperature, poured into water and extracted with methylene chloride. The combined organic phases are washed with water, dried over sodium sulfate and then concentrated (1.9 g solid). Flash chromatography (85/15 heptane/ethyl acetate) gives the expected product (1.5 g; 48% yield).

Workup

  1. temperatureThe medium is cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated (1.9 g solid)

Sources & evidence

ORD record
ord-90ea986a78e840c3a15e3213c4923d6b
Source dataset
uspto-grants-2014_02
Patent number
US08653134B2

Reaction notes

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