Dichloromethane → HCID 178486330, compound

HRID 1160842Notes

Reaction equation

HRID 1160842 reaction equation
[CH3:1][CH:2]([OH:40])[CH2:3][C:4]1[C:24]2=[C:25]3[C:7]([C:8]([CH:10]=[C:11]([O:35][CH3:36])[C:12]3=[C:13]3[C:23]4[C:18](=[C:19]([OH:32])[C:20]([O:30][CH3:31])=[C:21]([CH2:26][CH:27](O)[CH3:28])[C:22]=42)[C:16](=[O:17])[CH:15]=[C:14]3[O:33][CH3:34])=[O:9])=[C:6]([OH:37])[C:5]=1[O:38][CH3:39].ClCCl>CS(C)=O.C(OC(=O)C)(=O)C>[CH3:28][C:27]1[CH2:26][C:21]2[C:22]3[C:23]4[C:18]([C:19]([C:20]=2[O:30][CH3:31])=[O:32])=[C:16]([OH:17])[CH:15]=[C:14]([O:33][CH3:34])[C:13]=4[C:12]2[C:25]4[C:24]=3[C:4](=[C:5]([O:38][CH3:39])[C:6]([C:7]=4[C:8]([OH:9])=[CH:10][C:11]=2[O:35][CH3:36])=[O:37])[C:3]=1[C:2]([CH3:1])=[O:40]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 1303054,9-Dihydroxy-6,7-bis(2-hydroxypropyl)-1,5,8,12-tetramethoxyperylene-3,10-dione

Product 1

HCID 178486330HCID 178486330, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of Phleichrome (100 mg) in DMSO (2 mL) and acetic anhydride (1 mL) was heated at 40° C. for 24 h. The reaction mixture was diluted by dichloromethane (15 mL), washed with water and evaporated. The residue was chromatographed on two silica gel columns (1-5% MeOH-dichloromethane) to provide Hypocrellin B (25 mg, ˜25%). Thin-layer chromatography results and 1H-NMR were identical to that obtained from naturally occurring and extracted Hypocrellin B from H. bambusae, and as obtained by the two-step chemical conversion (Scheme 2).

Workup

  1. washwashed with water
  2. customevaporated
  3. customThe residue was chromatographed on two silica gel columns (1-5% MeOH-dichloromethane)

Sources & evidence

ORD record
ord-4ce41e89911e49b0b1d72db862e95566
Source dataset
uspto-grants-2010_10
Patent number
US07816563B1

Reaction notes

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