Benzaldehyde → 4-Methyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

HRID 714151Notes

Reaction equation

HRID 714151 reaction equation
[CH3:1][CH:2]([C:6](=[O:8])[CH3:7])[C:3](=[O:5])[CH3:4].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B(OCCCC)(OCCCC)O[CH2:19][CH2:20][CH2:21]C.[CH2:33](N)[CH2:34][CH2:35][CH3:36]>C(OCC)(=O)C>[CH3:1][CH:2]([C:6](=[O:8])[CH:7]=[CH:36][C:35]1[CH:21]=[CH:20][CH:19]=[CH:33][CH:34]=1)[C:3](=[O:5])[CH:4]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8007ButylamineHCID 12712Tributyl borateHCID 699493-Methyl-2,4-pentanedione

Product 1

HCID 695017264-Methyl-1,7-diphenyl-1,6-heptadiene-3,5-dioneYield 310%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boric anhydride (0.49 g, 7.0 mmol) was combined with 3-methyl-2,4-pentanedione (5, 1.14 g, 10.0 mmol) and stirred for 24 hr at room temperature under a nitrogen atmosphere. A solution of ethyl acetate (10 ml), benzaldehyde (1b, 2.05 ml, 20.2 mmol) and tributyl borate (11.0 ml, 40.5 mmol) was added and the mixture stirred for 15 min at room temperature. Butylamine (0.20 ml, 2.0 mmol) was added dropwise over 30 min and stirring was continued for 24 hr at room temperature. The resulting mixture was filtered to afford a solid. The crude solid was triturated with methanol to give 1.80 g (62%) of an orange solid: mp 154-157° C. [expected mp 154-157° C.]; 1H NMR: δ 2.17 (s, 3H), 7.12 (d, 2H, J=15.5 Hz), 7.38 (m, 6H), 7.58 (m, 4H), 7.74 (d, 2H, J=15.5 Hz); 13C NMR: δ 12.1, 106.2, 120.8, 182.1, 128.8, 129.9, 135.4, 141.3, 182.4. Anal. Calcd for C20H18O2: C, 82.73; H, 6.25. Found: C, 82.69; H, 6.36.

Workup

  1. stirringthe mixture stirred for 15 min at room temperature
  2. stirringstirring
  3. waitwas continued for 24 hr at room temperature
  4. filtrationThe resulting mixture was filtered
  5. customto afford a solid
  6. customThe crude solid was triturated with methanol

Sources & evidence

ORD record
ord-a3c8df7fc79a45f987c39c4fec0a70ac
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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