Ethanol → 1-(4-Allyloxy-5-iodo-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

HRID 1085629Notes

Reaction equation

HRID 1085629 reaction equation
[CH2:1]([O:4][C:5]1[C:12]([I:13])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])[CH:2]=[CH2:3].[CH:16]([C:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)=[O:19])=[CH2:17].C(O)C>S1C=CN=C1.C(N(CC)CC)C>[CH2:1]([O:4][C:5]1[C:12]([I:13])=[CH:11][C:8]([C:9](=[O:10])[CH2:17][CH2:16][C:18]([C:20]2[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=2)=[O:19])=[CH:7][C:6]=1[O:14][CH3:15])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 4382547Benzaldehyde, 3-iodo-5-methoxy-4-(2-propenyloxy)-HCID 104435242-Propen-1-one, 1-(3,4,5-trimethoxyphenyl)-

Product 1

HCID 157180261-(4-Allyloxy-5-iodo-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

Reagents, catalysts & solvents 2

HCID 9256ThiazoleCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-allyloxy-5-iodo-3-methoxybenzaldehyde (46 g, 0.15 mol), 3,4,5-trimethoxyphenyl vinyl ketone (38 g, 0.16 mol) and thiazole catalyst (6 g, 0.07 mol) in triethylamine (200 ml) was heated, with stirring, at 70° C. for 2 hours, and kept at room temperature overnight. Ethanol was added to the solid mass, filtered, and the filtrate was evaporated to a residue, which was purified by HPLC (hexane-ethyl acetate; 2:1, v/v) to afford 1-(4-allyloxy-5-iodo-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione, m.p. 113°-114° C.

Workup

  1. temperaturewas heated
  2. waitkept at room temperature overnight
  3. filtrationfiltered
  4. customthe filtrate was evaporated to a residue, which
  5. customwas purified by HPLC (hexane-ethyl acetate

Sources & evidence

ORD record
ord-fcca7019432445eaa6b9a4ac8bcbbd5a
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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