Dimethylformamide → 1-(5-Iodo-4-hydroxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

HRID 1085635Notes

Reaction equation

HRID 1085635 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:15][CH3:16])[C:9]=1[O:10][Si](C)(C)C)[CH:5]=[O:6].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][C:31](C=CC2C=C(OC)C(OC)=C(OC)C=2)=O)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26].C(N(CC)CC)C.CN(C=[O:58])C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[I:1][C:2]1[C:9]([OH:10])=[C:8]([O:15][CH3:16])[CH:7]=[C:4]([C:5](=[O:6])[CH2:31][CH2:30][C:29]([C:21]2[CH:20]=[C:19]([O:18][CH3:17])[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=2)=[O:58])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 3834051,5-Bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-oneHCID 157180253-Iodo-5-methoxy-4-[(trimethylsilyl)oxy]benzaldehyde

Product 1

HCID 157180331-(5-Iodo-4-hydroxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

Reagents, catalysts & solvents 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideCatalyst

Conditions

Temperature
70 °C

Procedure

To 3-iodo-4-trimethylsilyloxy-5-methoxybenzaldehyde in 570 mL of seive dried DMF was added 3,4,5-trimethoxyphenylvinyl ketone from Example 1, Step B (179 g, 0.805 mole) and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (61.9 g, 0.24 mole). Triethylamine (320 mL) was added, and the resulting mixture was stirred at 70° C. under nitrogen atmosphere for 2 hours. The mixture was cooled, filtered, and washed with MeOH (500 mL). The resulting solution was cautiously acidified with 6 N HCL to pH 1.5 and a heavy yellow precipitate began to form. This mixture was stirred at room temperature for 2 hours to ensure complete desilylation. The precipitate was filtered, washed with H2O (4×1 L), and redissolved in a minimum volume of CH2Cl2. The solution was washed with brine, dried over anhydrous MgSO4, and evaporated in vacuo to provide a white solid. The solid was washed with MeOH and dried under high vacuum to provide 1-(5-iodo-4-hydroxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-dione as a white solid, m.p. 189°-190° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washwashed with MeOH (500 mL)
  4. customto form
  5. stirringThis mixture was stirred at room temperature for 2 hours
  6. filtrationThe precipitate was filtered
  7. washwashed with H2O (4×1 L)
  8. dissolutionredissolved in a minimum volume of CH2Cl2
  9. washThe solution was washed with brine
  10. dry with materialdried over anhydrous MgSO4
  11. customevaporated in vacuo
  12. customto provide a white solid
  13. washThe solid was washed with MeOH
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-e9e309b1568243468fa200e65eddd2da
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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