Sodium Chloride → Broussonin B

HRID 1582721Notes

Reaction equation

HRID 1582721 reaction equation
[Na+].[Cl-].C[O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)=[C:9]([OH:11])[CH:10]=1.[CH3:22]C(C)=CCC1C=C2C(=CC=1O)OC(C1C=C(O)C=C(O)C=1)=C2>CO>[CH3:22][O:11][C:9]1[CH:10]=[C:5]([OH:4])[CH:6]=[CH:7][C:8]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 641376Moracin NHCID 5315502Broussonin A

Product 1

HCID 5315503Broussonin B

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Colorless needles; mp 88-89° C.; UV (MeOH) λmax (log ε) 266 (3.11), 239 (3.10) nm; IR (NaCl) γmax 3335, 2954, 1614, 1508, 1456 cm−1; 1H NMR (CD3OD, 300 MHz) δ 1.76 (2H, m, H-2), 2.49 (4H, m, H-1 and H-3), 3.74 (3H, s, OCH3), 6.29 (1H, dd, J=2.4 and 8.1 Hz, H-5′), 6.38 (1H, d, J=2.4 Hz, H-3′), 6.68 (2H, d, J=8.5 Hz, H-3″), 6.86 (1H, d, J=8.1 Hz, H-6′), 6.98 (2H, d, J=8.5 Hz, H-2″); 13C NMR (CD3OD, 75 MHz) δ 30.3 (C-1), 33.5 (C-2), 35.8 (C-3), 55.6 (OCH3), 99.7 (C-3′), 107.5 (C-5′), 116.0 (C-3″), 122.8 (C-1′), 130.3 (C-2″), 131.1 (C-6′), 134.8 (C-1″), 156.1 (C-4″), 157.6 (C-4′), 159.6 (C-2′); EIMS m/z 258 (M+, 52), 151 (18), 137 (100), 134 (20), 107 (48).

Sources & evidence

ORD record
ord-cd5b099041ea4607862561eb3ea620fa
Source dataset
uspto-grants-2004_05
Patent number
US06737439B2

Reaction notes

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