HCID 21474396, compound → HCID 21474331, compound

HRID 2294244Notes

Reaction equation

HRID 2294244 reaction equation
C(OC1C(=O)C=CN(CCO)C=1)C1C=CC=CC=1.C([O:26][C:27]1[C:32](=[O:33])[CH:31]=[CH:30][N:29]([CH2:34][CH2:35][OH:36])[C:28]=1[CH:37]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)[O:38]C1CCCCO1)C1C=CC=CC=1>C(O)C.Cl>[F:51][C:48]1[CH:47]=[CH:46][C:45]([CH:37]([OH:38])[C:28]2[N:29]([CH2:34][CH2:35][OH:36])[CH:30]=[CH:31][C:32](=[O:33])[C:27]=2[OH:26])=[CH:50][CH:49]=1

Participants

5

Reactant 2

HCID 21474396HCID 21474396, compoundHCID 86751617HCID 86751617, compound

Product 1

HCID 21474331HCID 21474331, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2-[4-Fluorophenyl)-hydroxy-methyl]-3-benzyloxy-1-(2-hydroxy-ethyl)-1H-pyridin-4-one: 13.7 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[(4-fluorophenyl)-(tetrahydropyran-2-yloxy)-methyl]-1H-pyridin-4-one are boiled under reflux for 3 hours in 150 ml of ethanol and 50 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 50 ml of ethyl acetate. Then, with stirring, 50 ml of 2N NaOH are added. The resulting product is filtered off and washed with water and ethyl acetate. After drying, 2-[(4-fluorophenyl)-hydroxy-methyl]-3-benzyloxy-1-(2-hydroxy-ethyl)-1H-pyridin-4-one remains, in the form of colourless crystals. M.p.: 187°-187.5° C.

Workup

  1. customthe ethanol is removed
  2. customa rotary evaporator
  3. additionThe residue is diluted with 50 ml of water
  4. addition50 ml of 2N NaOH are added
  5. filtrationThe resulting product is filtered off
  6. washwashed with water and ethyl acetate
  7. customAfter drying

Sources & evidence

ORD record
ord-1c98c1c691e640088b29c72c1ea58d4c
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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