Water → 5-(Methoxymethoxy)-6-nitroindane

HRID 1879403Notes

Reaction equation

HRID 1879403 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH2:10]2)=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].[CH3:14][O:15][CH2:16]Cl.O>CN(C=O)C>[CH3:14][O:15][CH2:16][O:13][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 130589616-Nitro-5-indanol

Product 1

HCID 583984775-(Methoxymethoxy)-6-nitroindane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

1.04 g of 55% sodium hydride/paraffin oil was suspended in 40.0 mL of DMF, and a solution of 3.90 g of 6-nitroindan-5-ol in DMF (10.0 mL) was added dropwise thereto at 5° C. over 15 minutes, followed by stirring at 5° C. for 30 minutes. To the reaction liquid was added dropwise 2.15 mL of methoxymethyl chloride over 5 minutes, followed by stirring at room temperature for 1 hour. To the reaction liquid was added water, followed by extraction with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20) to obtain 4.20 g of 5-(methoxymethoxy)-6-nitroindane.

Workup

  1. customTo the reaction liquid
  2. stirringby stirring at room temperature for 1 hour
  3. customTo the reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-9a362898f1e543ec947a8ee89da5419c
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

Loading…