Dimethylformamide → HCID 14742742, compound

HRID 1651221Notes

Reaction equation

HRID 1651221 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH:11]=1)[CH2:7][CH2:8][CH3:9].CN(C)[CH:24]=[O:25]>ClCCl>[CH2:6]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[CH2:13][CH2:12][C:11]=1[CH:24]=[O:25])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 14742741HCID 14742741, compound

Product 1

HCID 14742742HCID 14742742, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Phosphorus oxychloride (16.6 mL) was added dropwise with stirring to dimethylformamide (70 mL) at -5° C. After the addition was completed, the mixture was stirred at 0° C. for 15 minutes, then a solution of 1-butyl-3,4-dihydro-6-methoxy-naphthalene (34.9 g) in dimethylformamide (30 mL) was added slowly over 15 minutes while the reaction temperature was maintained at 0° C. The cooling bath was then withdrawn and after the mixture had stirred at room temperature for 1.5 hours, a few chips of ice were added, followed, after 5 minutes, by 10N sodium hydroxide (200 mL). The reaction was heated to 110° C. which caused the vigorous evolution of dimethylamine from the mixture and after 10 minutes the reaction was cooled, diluted with water (750 mL) and extracted with dichloromethane (1×500 mL; 2×300 mL). The organic layers were washed in turn with water (2×200 mL), then were combined, dried (MgSO4 ) and evaporated to furnish an amber oil which was passed through a short column of silica gel (200 g) in dichloromethane. The fractions containing the product were evaporated to yield 39.4 g of crude 1-butyl-3,4-dihydro-6-methoxy-2-naphthalene-carboxaldehyde as an oil.

Workup

  1. additionAfter the addition
  2. temperaturewas maintained at 0° C
  3. customThe cooling bath was then withdrawn
  4. stirringafter the mixture had stirred at room temperature for 1.5 hours
  5. additiona few chips of ice were added
  6. waitfollowed, after 5 minutes, by 10N sodium hydroxide (200 mL)
  7. temperatureThe reaction was heated to 110° C. which
  8. temperatureafter 10 minutes the reaction was cooled
  9. additiondiluted with water (750 mL)
  10. extractionextracted with dichloromethane (1×500 mL; 2×300 mL)
  11. washThe organic layers were washed in turn with water (2×200 mL)
  12. dry with materialdried (MgSO4 )
  13. customevaporated
  14. customto furnish an amber oil which
  15. additionThe fractions containing the product
  16. customwere evaporated

Sources & evidence

ORD record
ord-1725304c2e9e4ff3875516f0fff9bc6c
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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