Dimethylformamide → HCID 22152297, compound

HRID 1111330Notes

Reaction equation

HRID 1111330 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6]2.CN(C)[CH:16]=[O:17]>CCCCCC>[CH3:12][C:8]1([CH3:13])[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([CH:16]=[O:17])[CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 221522852,3-Dihydro-5-methoxy-1,1-dimethyl-1H-indene

Product 1

HCID 22152297HCID 22152297, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 10.60 g (60.0 mmol) of 5-methoxy-1,1-dimethylindane (see U.K. Patent Application No. GB 2,067,195 A for a method of obtaining this compound) and 6.5 g (90.0 mmol) of dimethylformamide was added 11.5 g (75.0 mmol) of phosphorous oxytrichloride. The mixture was heated at 100° C. for 5 h. The reaction mixture was cooled to ambient temperature and poured onto 100 g of ice. The aqueous residue was extracted with ether. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on silica gel (70 g) using a gradient from hexane to 2:98 (v/v) ether:hexane as eluent, There was obtained 4.86 g (23.8 mmol, 40%) of 1,1-dimethyl-5-methoxyindan-6-carboxaldehyde as a white solid after crystallization from hexane mp 51°-52° C.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe aqueous residue was extracted with ether
  3. washThe organic phase was washed with saturated sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (70 g)

Sources & evidence

ORD record
ord-ff500adc42bf472cbc712eddebb9f8bb
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

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