HCID 21474253, compound → HCID 21474409, compound

HRID 2294265Notes

Reaction equation

HRID 2294265 reaction equation
[CH2:1]([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]([O:25]C1CCCCO1)[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.Cl>[CH2:1]([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:25])[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21474253HCID 21474253, compound

Product 1

HCID 21474409HCID 21474409, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

3-Benzyloxy-1-(2-hydroxy-etbyl)-2-(hydroxy-thiophen-2-yl-methyl)-1H-pyridin-4-one: 1.88 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-[(tetrahydro-pyran-2-yloxy)-thiophen-2-yl-methyl]-1H-pyridin-4-one are boiled under reflux for 90 minutes in 7 ml of methanol and 4.25 ml of 2N hydrochloric acid. For working-up, the methanol is removed using a rotary evaporator. The residue is diluted with 20 ml of water and covered with 20 ml of ethyl acetate. Then, with stirring, 10 ml of saturated sodium hydrogen carbonate solution are added. The resulting product is filtered off and washed with water and ethyl acetate. Drying yields 3-benzyloxy-1-(2-hydroxy-ethyl)-2-(hydroxy-thiophen-2-yl-methyl)-1H-pyridin-4-one in the form of colourless crystals. M.p.: 193.8°-196° C.

Workup

  1. customthe methanol is removed
  2. customa rotary evaporator
  3. additionThe residue is diluted with 20 ml of water
  4. addition10 ml of saturated sodium hydrogen carbonate solution are added
  5. filtrationThe resulting product is filtered off
  6. washwashed with water and ethyl acetate
  7. customDrying

Sources & evidence

ORD record
ord-fd999b912ad640f98c1b6e30ab1f603b
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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