HCID 21474294, compound → HCID 10220846, compound

HRID 2294240Notes

Reaction equation

HRID 2294240 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C1C=CC=CC=1.C(OC1C(=O)C=CN(CCO)C=1C(C1C=CC=CC=1)OC1CCCCO1)C1C=CC=CC=1>C(O)C.Cl>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 21474294HCID 21474294, compoundHCID 21474354HCID 21474354, compound

Product 1

HCID 10220846HCID 10220846, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Benzyloxy-1-(2-hydroxy-ethyl)-2-(hydroxy-phenyl-methyl)-1H-pyridin-4-one: 3.39 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[phenyl-(tetrahydropyran-2-yloxy)-methyl]-1H-pyridin-4-one are boiled under reflux for 3 hours in 40 ml of ethanol and 10 ml of 2N HCl. For working-up, the ethanol is removed using a rotary evaporator. The residue is diluted with 50 ml of water and covered with 10 ml of ethyl acetate. Then, with stirring, 25 ml of saturated aqueous sodium hydrogen carbonate solution are added. The resulting product is filtered off and washed with water and ethyl acetate. After drying, 3-benzyloxy-1-(2-hydroxy-ethyl)-2-(hydroxy-phenyl-methyl)-1H-pyridin-4-one remains, in the form of colourless crystals. M.p.: 191.5°-192.5° C.

Workup

  1. customthe ethanol is removed
  2. customa rotary evaporator
  3. additionThe residue is diluted with 50 ml of water
  4. addition25 ml of saturated aqueous sodium hydrogen carbonate solution are added
  5. filtrationThe resulting product is filtered off
  6. washwashed with water and ethyl acetate
  7. customAfter drying

Sources & evidence

ORD record
ord-b7ea848edea14faeb67331462debc575
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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