Methanol → 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

HRID 1582720Notes

Reaction equation

CC(C)=CCC1C=C([C:12]2[O:22][C:21]3[CH:20]=[C:19]([OH:23])[CH:18]=[C:17](O)[C:16]=3[C:14](=[O:15])[C:13]=2[OH:25])C=CC=1O.CC1[CH2:41][C@@H:40]2[C:42]3C=CC(O)=CC=3O[C@]3(C4C=CC(O)=CC=4O)[CH:39]2[C@@H:30]([C:31]2[C:32]([OH:68])=[CH:33][C:34](C4OC5C=C(O)C=CC=5C=4)=[CH:35][C:36]=2[O:37]3)C=1.C[OH:70]>>[CH3:41][C:40]([CH3:42])=[CH:39][CH2:30][C:31]1[C:36]([OH:37])=[CH:35][C:34]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([OH:23])=[C:18]([OH:70])[CH:17]=3)=[C:13]([OH:25])[C:12](=[O:22])[C:33]=2[C:32]=1[OH:68]

Participants

Reactant 3

HCID 887Methanol

HCID 5318585Isolicoflavonol

HCID 44567218Albanol A

Product 1

HCID 54819662-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

Procedure

Yellow powder; UV (MeOH) λmax (log ε) 261 (4.13), 205 (4.79) nm; 1H NMR (CD3COCD3, 500 MHz) δ 1.66 (3H, s, H-5′), 1.82 (3H, s, H-4′), 3.56 (2H, d, J=6.0 Hz, H-1′), 5.29 (1H, m, H-2′), 6.36 (1H, s, H-8), 7.00 (1H, d, J=8.3 Hz, H-5′), 7.72 (1H, brd, J=7.4 Hz, H-6′), 7.87 (1H, s, H-2′); EIMS m/z 370 (M+, 100), 355 (94), 315 (45), 302 (37), 244 (12), 137 (21).

Sources & evidence

ORD record: ord-b128c2a8195d4663b463235d84746783
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737439B2

Reaction notes

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