Sodium Chloride → 2H-1-Benzopyran-7-ol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2S)-

HRID 1582719Notes

Reaction equation

HRID 1582719 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>CO>[OH:4][C:5]1[CH:10]=[C:9]2[C:8]([CH2:12][CH2:13][C@@H:14]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[O:11]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 5315502Broussonin A

Product 1

HCID 1582802H-1-Benzopyran-7-ol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2S)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Brown powder; mp 110-111° C.; [α]D20 −55.0° (c 0.02, MeOH); UV (MeOH) λmax (log ε) 282 (3.25), 223 (3.84), 204 (4.38) nm; CD (MeOH) nm Δε276.5 −11.0; IR (NaCl) γmax 3348, 2927, 1507, 1456 cm−1; 1H NMR (CD3OD, 300 MHz) δ 1.99 (1H, m, H-3), 2.09 (1H, m, H-3), 2.67 (1H, m, H-4), 2.86 (1H, m, H-4), 4.91 (1H, overlapped, H-2), 6.24 (1H, d, J=2.4 Hz, H-8), 6.30 (1H, dd, J=2.4 and 8.2 Hz, H-6), 6.77 (2H, d, J=8.6 Hz, H-3′), 6.85 (1H, d, J=8.2 Hz, H-5), 7.22 (2H, d, J=8.6 Hz, H-2′) EIMS m/z 242 (M+, 100), 149 (18), 136 (23), 123 (62) 120 (89).

Sources & evidence

ORD record
ord-6b56a86134b64a2f98dbe29b47203ece
Source dataset
uspto-grants-2004_05
Patent number
US06737439B2

Reaction notes

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