1-Bromopropane → 1-(3-Iodo-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

HRID 1085636Notes

Reaction equation

HRID 1085636 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[I:5][C:6]1[C:7]([OH:32])=[C:8]([O:30][CH3:31])[CH:9]=[C:10]([C:12](=[O:29])[CH2:13][CH2:14][C:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)=[O:16])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:5][C:6]1[C:7]([O:32][CH2:1][CH2:2][CH3:3])=[C:8]([O:30][CH3:31])[CH:9]=[C:10]([C:12](=[O:29])[CH2:13][CH2:14][C:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)=[O:16])[CH:11]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 157180331-(5-Iodo-4-hydroxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

Product 1

HCID 157180281-(3-Iodo-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

n-Propyl bromide (29.2 mL, 0.32 mole) was added to a solution of 1-(5-iodo-4-hydroxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione (100 g, 0.2 mole) in DMF (400 mL) containing potassium carbonate (96 g, 0.35 mole). The mixture was stirred at 70° C. for 2 hours during which time starting material disappeared. The mixture was cooled, filtered, and extracted with ethyl acetate, and the extract was washed with water and brine, dried over anhydrous MgSO4, and evaporated in vacuo to afford the crude product. Crystallization from ether/hexane gave the title compound as white crystals, m.p. 120°-121° C. NMR (CDCl3) δ 1.08 (t, J=7.5 Hz, CH2CH2CH3) 1.87 (m, CH2CH2CH3), 2.41 (t, J=4 Hz, COCH2CH2CO), 3.90 and 3.94 (s, u Ar OCH3), 4.04 (t, J=8 Hz, OCH2CH2CH3), 7.28 (s, trimethoxyphenyl H-2, H-6), 7.51 (d, J=1.5 Hz, Iodophenyl 'H-6), 8.06 (d, J=1.5 Hz, Iodophenyl 'H-2).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated in vacuo
  7. customto afford the crude product
  8. customCrystallization from ether/hexane

Sources & evidence

ORD record
ord-ef0db20f7803405aa080239b2cf970a0
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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