Water → 4-[3,4-Dimethoxy-2-(3-methoxy-2,2-dimethyl-propoxy)-phenyl]-indan-1-one

HRID 2171055Notes

Reaction equation

HRID 2171055 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C:16]2=[O:21].Br[CH2:23][C:24]([CH3:29])([CH3:28])[CH2:25][O:26][CH3:27].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:9][O:8][C:7]1[C:2]([O:1][CH2:23][C:24]([CH3:29])([CH3:28])[CH2:25][O:26][CH3:27])=[C:3]([C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][C:16]3=[O:21])[CH:4]=[CH:5][C:6]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 649954481-Bromo-3-methoxy-2,2-dimethylpropaneHCID 674668064-(2-Hydroxy-3,4-dimethoxy-phenyl)-indan-1-one

Product 1

HCID 674677154-[3,4-Dimethoxy-2-(3-methoxy-2,2-dimethyl-propoxy)-phenyl]-indan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Compound 303 (0.02 g, 0.07 mmol) and 1-bromo-3-methoxy-2,2-dimethyl-propane (0.12 g, 0.56 mmol) were dissolved in dry DMF (0.8 mL). K2CO3 (0.1 g, 0.68 mmol) were added. The suspension was heated at 100° C. for 18 h. H2O was added and the mixture was extracted with EtOAc (×2). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by preparative HPLC afforded the title compound as an oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-d03a410ef7f24d4cb26aafa49bfa414f
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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