Potassium Carbonate → 6-Methoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one

HRID 460345Notes

Reaction equation

HRID 460345 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.Cl[CH2:15][CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:13])=[CH:3][C:2]=1[O:1][CH2:15][CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2549542-(3-Chloropropoxy)oxane2×HCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one2×

Product 1

HCID 184458196-Methoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-Hydroxy-6-methoxy-indan-1-one (Intermediate H, 2.98 g, 0.017 mole), 2-(3-chloro-propoxy)-tetrahydro-pyran (Compound 18a) (6.0 g, 0.034 mole), and potassium carbonate (10.0 g, 0.0725 mole) were stirred in 50 mL of DMF at 80° C. overnight under Argon. The reaction mixture was then diluted with 200 mL of ethyl acetate and washed 3 times with water. After drying over sodium sulfate, the solvent was removed in vacuo. The crude material solidified on standing to yield the title compound, 6-Methoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one. MS m/z 309 (M+H)+.

Workup

  1. washwashed 3 times with water
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c9e3a7d634514e7bb246c7c0effdd39a
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Reaction notes

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