Heptane → HCID 67034856, compound

HRID 1035854Notes

Reaction equation

HRID 1035854 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[OH:19])=[O:8].[CH3:20]CCCCCC>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:7](=[O:8])[C:9]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=2)[O:19][CH:20]=1

Participants

4

Reactant 2

HCID 8900HeptaneHCID 51347972HCID 51347972, compound

Product 1

HCID 67034856HCID 67034856, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2nd method: A solution of 500 mg (1.5 mmol) of the compound of the above Step, 6-bromo-1-(2-hydroxy-4,5-dimethoxyphenyl)-hexan-1-one, in 30 ml of dry toluene is refluxed, with stirring, with 0.6 ml (4.5 mmol) of DMF dimethylacetal. Reflux is continued for 5 h. After concentration, and purification by flash chromatography with a gradient of pure heptane to heptane-ACOEt 80-20, 270 mg (yield=53%) of 3-(4-bromobutyl)-6,7-dimethoxychromen-4-one are obtained, after evaporation, in the form of white crystals identical to those obtained by the 1st method. TLC SiO2 hept-AcOEt 70-30 Rf=0.3. 1H NMR (DMSO): 8.19 (s, 1H), 7.36 (s, 1H), 7.16 (s, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.65 (t, 2H, J=6.3 Hz), 2.38 (t, 2H, J=7.3 Hz), 1.72 (m, 2H), 1.64 (m, 2H), 1.55 (m, 2H).

Workup

  1. temperatureReflux

Sources & evidence

ORD record
ord-7f78fcbfcaa141508a79fba0879bb122
Source dataset
uspto-grants-2013_10
Patent number
US08546402B2

Reaction notes

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