Methanol → Broussonin A

HRID 1582717Notes

Reaction equation

[Na+].[Cl-].CC1C[C@@H]2C3C=CC(O)=CC=3O[C@:14]3([C:26]4[CH:27]=[CH:28][C:29]([OH:33])=[CH:30][C:31]=4O)[CH:15]2[C@@H:6]([C:7]2[C:8]([OH:44])=[CH:9][C:10](C4OC5C=C(O)C=CC=5C=4)=[CH:11][C:12]=2O3)C=1.[CH3:45][OH:46]>>[CH3:45][O:46][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:15][CH2:14][C:26]2[CH:27]=[CH:28][C:29]([OH:33])=[CH:30][CH:31]=2)=[C:8]([OH:44])[CH:9]=1

Participants

Reactant 3

HCID 887Methanol

HCID 5234Sodium Chloride

HCID 44567218Albanol A

Product 1

HCID 5315502Broussonin A

Procedure

Yellow powder; mp 95-96° C.; UV (MeOH) λmax (log ε) 279 (3.67), 231 (3.82) nm; IR (NaCl) γmax 3380, 1625, 1558, 1507 cm 1; 1H NMR (CD3OD, 500 MHz) δ 1.78 (2H, m, H-2), 2.51 (4H, m, H-1 and H-3), 3.71 (3H, s, OCH3), 6.31 (1H, dd, J=2.5 and 8.1 Hz, H-5′), 6.33 (1H, d, J=2.4 Hz, H-3′), 6.67 (2H, d, J=8.6 Hz, H-3″), 6.90 (1H, d, J=8.2 Hz, H-6′), 6.98 (2H, d, J=8.5 Hz, H-2″); 13C NMR (CD3OD, 125 MHz) δ 30.3 (C-1), 33.5 (C-2), 35.9 (C-3), 55.6 (OCH3), 102.3 (C-3′), 105.4 (C-5′), 116.0 (C-3″), 122.5 (C-1′), 130.3 (C-2″), 131.4 (C-6′), 134.9 (C-1″), 156.2 (C-4″), 157.0 (C-2′), 160.3 (C-4′); EIMS m/z 258 (M+, 62), 151 (21), 137 (100), 107 (26).

Sources & evidence

ORD record: ord-784ad9a04e574e1b972f8b3f8b358bc5
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737439B2

Reaction notes

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