Dimethylformamide → HCID 10800448, compound

HRID 355347Notes

Reaction equation

HRID 355347 reaction equation
[Mg].Br[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[CH:5][CH:4]=1.CN(C)[CH:21]=[O:22]>O1CCCC1.II>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[O:12][CH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([CH:21]=[O:22])[CH:11]=2)[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 5462224MagnesiumHCID 104942052H-Pyran, 2-[(6-bromo-2,3-dihydro-1H-inden-1-yl)oxy]tetrahydro-

Product 1

HCID 10800448HCID 10800448, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

A mixture of magnesium (228 mg) and iodine (3 mg) in tetrahydrofuran (3 ml) is heated at 60° C. under argon atmosphere, and thereto is added dropwise with stirring a solution of 6-bromo-1-tetrahydropyranyloxyindane (2.60 g) in tetrahydrofuran (5 ml). After addition, the mixture is stirred at 70° C. for one hour. To the mixture is added dropwise a solution of dimethylformamide (959 mg) in tetrahydrofuran (2 ml) under ice-cooling, and the mixture is stirred under ice-cooling for one hour. The reaction solution is poured into a mixture of ice-acetic acid, and extracted with ethyl acetate. The extract is washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate) to give 1-tetrahydropyranyloxyindane-6-carbaldehyde (1081 mg).

Workup

  1. additionis added dropwise
  2. additionAfter addition
  3. temperaturecooling
  4. stirringthe mixture is stirred under ice-
  5. temperaturecooling for one hour
  6. extractionextracted with ethyl acetate
  7. washThe extract is washed with water
  8. customdried
  9. customevaporated
  10. customto remove the solvent
  11. customThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-febacd6a30d2404b802d1e9f1693c162
Source dataset
uspto-grants-1998_11
Patent number
US05830873

Reaction notes

Loading…