Dimethylformamide dimethyl acetal → Isoflavone

HRID 402858

Reaction equation

HRID 402858 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])=[CH:5][CH:4]=1.[CH3:18][O:19]C(OC)N(C)C>C1COCC1>[O:19]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:3][CH:4]=2)[C:9](=[O:10])[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:18]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-one

Product 1

HCID 72304IsoflavoneYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To an oven-dried microwave vial was added 4-methoxydeoxybenzoin (73 mg, 2.83 mmol), dimethyl formamide dimethyl acetal (0.188 mL, 1.41 mmol) and THF (0.100 mL). The reaction was heated to 120° C. for 2 min. The product was recrystallized from methanol and a few drops of water to afford 12 (50 mg, 66%) as a pink powder. Analytical data for isoflavone 12: 1H NMR (500 MHz, DMSO) δ 9.56 (s, 1H), 8.38 (s, 1H), 8.03 (d, J=9 Hz, 1H), 7.40 (d, J=9 Hz, 2H), 7.16 (s, 1H), 7.08 (d, J=9 Hz, 1H), 6.81 (d, J=9 Hz, 2H), 3.91 (s, 3H); 13C NMR (125 MHz, DMSO) δ 175.4, 164.3, 158.1, 157.9, 153.9, 130.8, 127.6, 124.4, 123.0, 118.3, 115.7, 115.4, 101.2, 56.8; LCMS: Mass calculated for C16H12O4, [M+H]+, 269. Found 269.

Workup

  1. customThe product was recrystallized from methanol and a few drops of water

Sources & evidence

ORD record
ord-6e9905dadb04473195a893b13bcd8097
Source dataset
uspto-grants-2014_06
Patent number
US08742141B2

Linked notes

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