Dimethylformamide → HCID 12847535, compound

HRID 1527710Notes

Reaction equation

HRID 1527710 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH3:16].[Li]CCCC.CN([CH:25]=[O:26])C>C1COCC1>[CH3:14][O:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[C:4]([O:15][CH3:16])[C:5]=1[CH:25]=[O:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 64311191,2,4-trimethoxynaphthaleneHCID 178418339Butyllithium

Product 1

HCID 12847535HCID 12847535, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure by Syper et al.,38 100 (1.07 g, 4.90 mmol) was dissolved in THF (20.0 mL) at 0° C. under Argon, and then nBuLi (1.6 M in hexanes, 4.0 mL, 10.0 mmol) was added at 0° C. The reaction was stirred at 0° C. for 5 hours before DMF (0.850 mL, 11.0 mmol) was added at 0° C. The reaction was stirred for another 30 minutes at room temperature before quenching with water. The reaction was diluted with ethyl ether and washed with saturated brine. The organic layer was dried over MgSO4, filtered, and condensed. Crude product was used as a 5:1 mixture of product:starting material, affording 54 (1.07 g, 4.35 mmol, 89%) as a yellow oil. Following purification via column chromatography (CH2Cl2 to 1:9 EtOAc:CH2Cl2) pure aldehyde 54 was obtained as a yellow solid.

Workup

  1. additionwas added at 0° C
  2. custombefore quenching with water
  3. additionThe reaction was diluted with ethyl ether
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customcondensed
  8. additionCrude product was used as a 5:1 mixture of product

Sources & evidence

ORD record
ord-c2990d7c5fc843099f74e145b1d4fbf3
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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