Water → HCID 68549850, compound

HRID 77667Notes

Reaction equation

HRID 77667 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:22])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=2)=[CH:4][C:3]=1[O:23][CH3:24].[C:25](OC(=O)C)(=[O:27])[CH3:26].N1[CH:37]=[CH:36]C=CC=1.[OH2:38]>>[C:25]([O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]=[CH:11][C:10](=[O:22])[CH:9]=[CH:8][C:5]2[CH:6]=[CH:7][C:2]([O:1][C:36](=[O:38])[CH3:37])=[C:3]([O:23][CH3:24])[CH:4]=2)=[CH:14][C:15]=1[O:20][CH3:21])(=[O:27])[CH3:26]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 4681331,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

Product 1

HCID 68549850HCID 68549850, compoundYield 88%

Procedure

1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one (20a, 0.32 g, 1.0 mmol) was dissolved in acetic anhydride (21, 7.00 ml, 74.1 mmol) and stirred for 5 min at room temperature. Pyridine (0.70 ml, 8.7 mmol) was added and the mixture stirred for 30 min at 100° C. The resulting mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from tetrahydrofuran/hexane to give 0.36 g (88%) of a yellow solid: mp 179-180° C. [expected mp 150° C.]; 1H NMR: δ 2.31 (s, 6H), 3.87 (s, 6H), 6.98 (d, 2H, J=15.9 Hz), 7.06 (d, 2H, J=8.1 Hz), 7.18 (m, 4H), 7.67 (d, 2H, J=15.9 Hz); 13C NMR: δ 20.7, 56.0, 111.7, 121.4, 123.3, 125.5, 133.7, 141.6, 142.6, 151.4, 168.5, 188.3; Exact mass calcd for C23H22O7: 410.1366, observed (M+H) 411.1444.

Workup

  1. stirringthe mixture stirred for 30 min at 100° C
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-8287612ed49e4196ada94f583a496827
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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