Hydrochloric Acid → HCID 71607581, compound

HRID 714493

Reaction equation

HRID 714493 reaction equation
[CH:1]1[C:6]([C@@H:7]2[O:16][C:15]3[CH:14]=[C:13]([OH:17])[CH:12]=[C:11]([OH:18])[C:10]=3[CH2:9][C@@H:8]2[OH:19])=[CH:5][C:4]([OH:20])=[C:3]([OH:21])[CH:2]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1[CH:34]=[CH:33]C=CC=1.Cl.CN(C=[O:40])C>>[C:22]([O:21][C:3]1[CH:2]=[CH:1][C:6]([C@@H:7]2[C@H:8]([OH:19])[CH2:9][C:10]3[C:15](=[CH:14][C:13]([OH:17])=[CH:12][C:11]=3[OH:18])[O:16]2)=[CH:5][C:4]=1[O:20][C:33](=[O:40])[CH3:34])(=[O:24])[CH3:23]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 182232(+)-Epicatechin

Product 1

HCID 71607581HCID 71607581, compound

Procedure

To a stirred solution of (±) epicatechin 1 (0.10 gm, 0.34 mmol) in DMF, Acetic anhydride (0.11 ml, 0.10 mmol) and pyridine (0.08 ml, 0.10 mmol) was added at room temperature. After an additional stirring at this for 24 h, 2N HCl was added and extracted with ethyl acetate (2×50 ml). The combined organic layer was washed with brine and dried over sodium sulphate. The crude reaction mixture was purified using preparative HPLC to afford 4-((2R,3R)-3,5,7-trihydroxychroman-2-yl)-1,2-phenylene diacetate (0.004 gm) and 4-((2R,3R)-3,5,7-trihydroxychroman-2-yl)-1,2-phenylene diacetate (0.008 gm) as a white solid material.

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulphate
  4. customThe crude reaction mixture
  5. customwas purified

Sources & evidence

ORD record
ord-48edf0783c39400e824884187be41586
Source dataset
uspto-grants-2015_11
Patent number
US09187448B2

Linked notes

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