Dimethylformamide → 3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-2,4-dimethoxy-benzaldehyde

HRID 1057843Notes

Reaction equation

HRID 1057843 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]3([CH3:23])[CH3:22])[C:7]=1[O:8][CH3:9].CN(C)[CH:28]=[O:29]>C1COCC1>[CH3:21][C:16]1([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]2[CH:11]=[C:10]([C:6]3[C:7]([O:8][CH3:9])=[C:2]([CH:3]=[CH:4][C:5]=3[O:24][CH3:25])[CH:28]=[O:29])[CH:19]=[CH:18][C:17]1=2

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 694617116-(5-Bromo-2,6-dimethoxyphenyl)-1,1,4,4-tetramethy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 222683493-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-2,4-dimethoxy-benzaldehydeYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-(5-bromo-2,6-dimethoxyphenyl)-1,1,4,4-tetramethy-1,2,3,4-tetrahydronaphthlene (0.24 g, 0.55 mmol) in anhydrous THF (6 mL) was added at −78° C. under argon n-BuLi (1.6 M in hexane, 0.7 mL, 1.1 mmol). The solution was stirred for 5 minutes at −78° C. and N,N-dimethylformamide (0.13 mL, 1.65 mmol) was added. The reaction mixture was stirred 2 hours at −78° C. then quenched with aqueous ammonium chloride and brought to room temperature. The solution was diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed and silica gel (eluent: ethyl acetate/hexane, 1:9) to give 0.14 g (72%) of 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-2,4-dimethoxy-benzaldehyde. 1H NMR (500 MHz; CDCl3): δ1.29 (s, 6H); 1.32 (s, 6H); 1.72 (s, 4H); 3.37 (s, 3H); 3.83 (s, 3H); 6.83 (d, J=9.0 Hz, 1H); 7.14 (dd, J1=2.0 Hz, J2=8.5 Hz, 1H); 7.33 (d, J=8.0 Hz, 1H); 7.36 (s, 1H); 7.85 (d, J=8.5 Hz, 1H); 10.29 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred 2 hours at −78° C.
  2. customthen quenched with aqueous ammonium chloride
  3. custombrought to room temperature
  4. additionThe solution was diluted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed

Sources & evidence

ORD record
ord-52e13e621da54f93ad81dbcca4ea216b
Source dataset
uspto-grants-2003_02
Patent number
US06515003B1

Reaction notes

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