Sodium Chloride → Broussochalcone B

HRID 1582722Notes

Reaction equation

HRID 1582722 reaction equation
[Na+].[Cl-].[CH3:3][C:4]([CH3:25])=[CH:5][CH2:6]C1C(O)=CC(O)=CC=1C1OC2C=C(O)C=CC=2C=1.CC(C)=CC[C:30]1[CH:31]=[C:32]([C:37]2O[C:46]3[CH:45]=[C:44]([OH:48])[CH:43]=[C:42]([OH:49])[C:41]=3[C:39](=[O:40])[C:38]=2O)[CH:33]=[CH:34][C:35]=1[OH:36]>CO>[CH3:3][C:4]([CH3:25])=[CH:5][CH2:6][C:45]1[CH:46]=[C:41]([C:39](/[CH:38]=[CH:37]/[C:32]2[CH:33]=[CH:34][C:35]([OH:36])=[CH:30][CH:31]=2)=[O:40])[C:42]([OH:49])=[CH:43][C:44]=1[OH:48]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 641375Demethylmoracin IHCID 5318585Isolicoflavonol

Product 1

HCID 6450879Broussochalcone B

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Yellow powder; mp 157-158° C.; UV (MeOH) λmax (log ε) 373 (4.23), 205 (4.43) nm; IR (NaCl) γmax 3350, 2923, 1645, 1558, 1508 cm−1; 1H NMR (CD3OD, 500 MHz) δ 1.75 (3H, s, H-4″), 1.76 (3H, s, H-5″), 3.27 (2H, d, J=7.2 Hz, H-1″), 5.34 (1H, m, H-2″), 6.29 (1H, s, H-3′), 6.85 (2H, d, J=8.5 Hz, H-3), 7.54 (1H, d, J=15.4 Hz, H-a), 7.59 (2H, d, J=8.5 Hz, H-2), 7.72 (1H, s, H-6′), 7.76 (1H, d, J=15.3 Hz, H-β); 13C NMR (CD3OD, 125 MHz) δ 17.8 (C-4″), 26.0 (C-5″), 28.9 (C-1″), 103.4 (C-3′), 114.4 (C-1′), 117.0 (C-3), 118.6 (C-o), 122.2 (C-5′), 124.2 (C-2″), 127.4 (C-1), 131.9 (C-2), 132.4 (C-6′), 133.1 (C-3″), 145.4 (C-β), 161.5 (C-4), 164.6 (C-4′), 165.5 (C-2′), 193.4 (CO); EIMS m/z 324 (M+, 100), 231 (10), 205 (77), 147 (12).

Sources & evidence

ORD record
ord-402edb9dfc7a4e77adecf815e400fcbb
Source dataset
uspto-grants-2004_05
Patent number
US06737439B2

Reaction notes

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