Potassium Carbonate → HCID 10689805, compound

HRID 431289Notes

Reaction equation

HRID 431289 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][CH:19](Br)[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31].[O-]S([O-])(=O)=O.[Mg+2]>C([O-])(O)=O.[Na+].CCOCC.CN(C=O)C>[CH3:18][CH:19]([O:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[CH3:10])[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 15438996HCID 15438996, compound

Product 1

HCID 10689805HCID 10689805, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

DMF (5 mL) at r.t. was added to a stirring mixture of 4-hydroxy-3,5-dimethylbenzaldehyde (116 mg, 0.78 mmol), potassium carbonate (214 mg, 1.55 mmol) and a-methyl-2-nitro-4,5-dimethoxybenzyl bromide (169 mg, 0.58 mmol) and stirring was continued for 44 hours. The reaction was diluted with 5% NaHCO3 (100 mL) and aqueous workup (Et2O, MgSO4) followed by concentration in vacuo yielded a yellow oil which was purified by flash chromatography (20 g, 5:1 hexanes/ethyl acetate) to yield 7e (125 mg, 60%) as a yellow oil: 1H NMR (270 MHz, CDCl3) d 1.56 (d, J=6.2 Hz, 3H), 2.22 (s, 6H), 3.92 (s, 3H), 4.01 (s, 3H), 5.83 (q, J=6.2 Hz, 1H), 7.49 s, 3H), 7.57 (s, 1H), 9.81 (s, 1H); 13C NMR (68 MHz, CDCI3) d 17.6, 23.5, 56.4, 56.5, 76.6, 107.5, 109.0, 131.1, 131.7, 132.1, 134.5, 139.0, 148.1, 153.8, 160.5, 191.5.

Workup

  1. concentrationfollowed by concentration in vacuo
  2. customyielded a yellow oil which
  3. customwas purified by flash chromatography (20 g, 5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f15d39428abc41e2ae41957a5772e12d
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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