Sodium Chloride → Moracin M

HRID 1582724Notes

Reaction equation

HRID 1582724 reaction equation
[Na+].[Cl-].CC(C)=CC[C:7]1[C:12]([OH:13])=[CH:11][C:10]([OH:14])=[CH:9][C:8]=1[C:15]1[O:23][C:22]2[CH:21]=[C:20]([OH:24])[CH:19]=[CH:18][C:17]=2[CH:16]=1>CO>[CH:18]1[C:17]2[CH:16]=[C:15]([C:8]3[CH:9]=[C:10]([OH:14])[CH:11]=[C:12]([OH:13])[CH:7]=3)[O:23][C:22]=2[CH:21]=[C:20]([OH:24])[CH:19]=1

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 641375Demethylmoracin I

Product 1

HCID 185848Moracin M

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Needles; UV (MeOH) λmax (log ε) 328 (4.36), 315 (4.44), 215 (4.45) nm; IR (NaCl) γmax 3339, 1612, 1442, 1292, 1151, 1000 cm−1; 1H NMR (CD3OD, 500 MHz) δ 6.25 (1H, t, J=2.2 Hz, H-4′), 6.73 (1H, dd, J=2.2, 8.4 Hz, H-5), 6.76 (2H, d, J=2.2 Hz, H-2′ and 6′), 6.90 (1H, d, J=1.8 Hz, H-7), 6.91 (1H, s, H-3), 7.34 (1H, d, J=8.3 Hz, H-4); 13C NMR (CD3OD, 125 MHz) δ 98.4 (C-7), 102.2 (C-3), 103.5 (C-4′), 103.9 (C-2′ and C-6′), 113.2 (C-5), 122.0 (C-4), 123.0 (C-9), 133.8 (C-1′), 156.1 (C-6), 156.8 (C-2), 157.2 (C-8), 159.9 (C-3′); EIMS m/z 242 (M+, 100), 213 (9), 121 (10).

Sources & evidence

ORD record
ord-eb042d598af6453a9bd8ab2e3eea74d2
Source dataset
uspto-grants-2004_05
Patent number
US06737439B2

Reaction notes

Loading…