Dimethylformamide → 4-Methoxy-5-(3-methoxy-propoxy)-2-methyl-benzaldehyde

HRID 1158457Notes

Reaction equation

HRID 1158457 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])[C:5]([O:14][CH3:15])=[CH:4][C:3]=1[CH3:16].CCCCCC.CN([CH:26]=[O:27])C>C1COCC1>[CH3:15][O:14][C:5]1[C:6]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:7][C:2]([CH:26]=[O:27])=[C:3]([CH3:16])[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8058HexaneHCID 59223954HCID 59223954, compound

Product 1

HCID 592239044-Methoxy-5-(3-methoxy-propoxy)-2-methyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-4-methoxy-5-(3-methoxy-propoxy)-2-methyl-benzene (2.50 g, 8.65 mmol) in THF (25 mL), cooled to −70° C., is added a 1.6M solution of n-buthyllithium in hexane (5.94 mL, 9.51 mmol). After 30 min, DMF (1.05 mL, 13.0 mmol) is added and stirring is continued overnight while the reaction mixture is gradually warmed to room temperature. Quenching with ice-cold 1N aqueous HCl is followed by extraction with diethyl ether. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 7:2) gives the title compound as oil. TLC, Rf (hexane/AcOEt 1:1)=0.29. MS: 239.2 [M+H]+. 1H-NMR (CDCl3): δ 2.16 (m, 2H), 2.66 (s, 3H), 3.39 (s, 3H), 3.60 (m, 2H), 3.97 (s, 3H), 4.18 (m, 2H), 6.73 (s, 1H), 7.40 (s, 1H), 10.2 (s, 1H) ppm.

Workup

  1. waitis continued overnight while the reaction mixture
  2. customQuenching with ice-cold 1N aqueous HCl
  3. extractionis followed by extraction with diethyl ether
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (hexane/AcOEt 7:2)

Sources & evidence

ORD record
ord-974b4b7482f14ff79432bb05e6100208
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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