Chloroform → HCID 69314550, compound

HRID 1754588Notes

Reaction equation

HRID 1754588 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([O:8][C@H:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:20])=[CH:15][C:16]=3[OH:19])[O:11][C@@H:10]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:28])[CH:22]=2)=[O:7])=[CH:4][CH:3]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[C:6]([OH:8])(=[O:7])[CH3:5].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][C@H:9]2[CH2:18][C:17]3[C:12](=[CH:13][C:14]([OH:20])=[CH:15][C:16]=3[OH:19])[O:11][C@@H:10]2[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:28])[CH:22]=2)=[O:7])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 69138977HCID 69138977, compound

Product 1

HCID 69314550HCID 69314550, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Under an N2 atmosphere, to a solution of (+)-(2R,3S)-5,7-dihydroxy-2-(3,4-dihydroxyphenyl)chroman-3-yl 4-hydroxybenzoate 11 (20 mg, 0.048 mmol) in pyridine (1 ml), acetic anhydride (0.2 ml) was added dropwise at 0° C. The reaction mixture was stirred at rt overnight. The excess pyridine was distilled under vacuum. The residue was purified by flash chromatograph on silica gel (EtOAc/n-hexane, 1/1 in v/v) to afford 22* (34 mg, 95% yield). mp: mp 149-151° C.; [α]D=+42.5 (c=1.2, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 7.96 9d, J=8.7 Hz, 2H), 7.31 (A of ABq, J=8.4, 1.8 Hz, 1H), 7.26 (d, J=1.8 Hz, 1H), 7.21 (B of AB, J=8.4 Hz, 1H), 7.15 (d, J=8.7 Hz, 2H), 6.70 (d, J=2.2 Hz, 1H), 6.63 (d, J=2.2 Hz, 1H), 5.51 (dd, J=11.2, 6.0 Hz, 1H), 5.33 (d, J=6.0 Hz, 1H), 3.04 (A of ABq, J=16.8, 5.0 Hz, 1H), 2.83 (B of ABq, J=16.8, 6.0 Hz, 1H), 2.31 (s, 3H), 2.29 (s, 3H), 2.28 (s, 3H), 2.27 (s, 6H); 13C NMR (CDCl3, 400 MHz): δ 168.8, 168.7, 168.3, 167.9, 164.8, 154.5, 154.3, 149.8, 149.4, 142.2, 142.1, 136.1, 131.3, 126.9, 124.3, 123.7, 122.0, 121.6, 121.3, 110.0, 108.7, 107.6, 77.7, 69.1, 23.9, 21.0, 20.7, 20.5; HRMS (ESI) calcd for C32H28O13Na (M+Na) 643.1428; found 643.1437.

Workup

  1. distillationThe excess pyridine was distilled under vacuum
  2. customThe residue was purified by flash chromatograph on silica gel (EtOAc/n-hexane, 1/1 in v/v)
  3. customto afford 22* (34 mg, 95% yield)

Sources & evidence

ORD record
ord-1c3963fa4a9e43b58e26a3f3535ff063
Source dataset
uspto-grants-2015_10
Patent number
US09169230B2

Reaction notes

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