Dimethylformamide → 4-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one

HRID 2171010Notes

Reaction equation

HRID 2171010 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:14]OC)=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:17](=[O:20])([O-])[O-].[Cs+].[Cs+].BrC1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][CH2:27][C:28]2=[O:33].CN(C)[CH:36]=[O:37]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][O:9][C:8]1[C:3]([O:2][CH2:1][O:20][CH3:17])=[C:4]([C:14]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH2:26][CH2:27][C:28]3=[O:33])[CH:5]=[CH:6][C:7]=1[O:37][CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 987131-Indanone, 4-bromo-HCID 67462911[3,4-Dimethoxy-2-(methoxymethyl)phenyl]boronic acid2×

Product 1

HCID 866775744-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

To a stirring solution 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid (Compound 301)(1 g, 0.186 mmol) in dimethylformamide under nitrogen atmosphere, were added cesium carbonate (4.5 g, 13.84 mmol), tetrakis(triphenylphosphine)palladium(0) (269 mg, 0.232 mmol) and 4-bromo-indan-1-one (1.35 g, 5.57 mmol) and the resultant reaction mixture was heated to 90° C. for 4 h. The reaction mixture was filtered off and the filtrate was extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-35% ethyl acetate in pet ether) afforded 4-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one as a solid.

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered off
  3. extractionthe filtrate was extracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (silica gel, 0-35% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-af4679a3b0d943abb89b4c2a832c028f
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…