Water → 5-[(R)-1-(tetrahydrofuran-2-yl)methoxy]-indan-1-one

HRID 69502

Reaction equation

HRID 69502 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[O:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17]OS(C)(=O)=O.O>CN(C=O)C>[O:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 2331475-Hydroxy-1-indanoneHCID 18649742HCID 18649742, compound

Product 1

HCID 689893065-[(R)-1-(tetrahydrofuran-2-yl)methoxy]-indan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-hydroxyindanone (80 mg) and methanesulfonic acid (R)-1-(tetrahydrofuran-2-yl)methyl ester (107 mg) in DMF (1 mL) was stirred at 70° C. for 16 h. After adding water it was extracted with ether, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. In this way the product was obtained with molecular weight 232.28 (C14H16O3); MS (ESI): 233 (M+H+).

Workup

  1. extractionwas extracted with ether
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel
  5. customIn this way the product was obtained with molecular weight 232.28 (C14H16O3)

Sources & evidence

ORD record
ord-7f3e6357e7c0499d9f9a3072dd89921e
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Linked notes

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