Acetic Acid → HCID 68130945, compound

HRID 1658812Notes

Reaction equation

HRID 1658812 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:23])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH:16]=[C:15]([C:18]3OC=C[N:22]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cr](O)(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].Cl.[C:36](O)(=[O:38])[CH3:37]>CO.CCOCC>[O:38]1[CH:36]=[CH:37][C:18]([C:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:23])[CH2:17][CH:16]=2)=[N:22]1

Participants

8

Reactant 5

HCID 176Acetic Acid2×HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24425Chromic AcidHCID 21505599HCID 21505599, compound

Product 1

HCID 68130945HCID 68130945, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 3283Diethyl EtherSolvent

Procedure

A 1.58 g. portion of 3,6-dihydro-α-(p-fluorophenyl)-4-(2-oxazolyl)-1(2H)-pyridinebutanol, prepared as described in Example 15, in 45 ml. of acetic acid is stirred at room temperature. A 30 ml. portion of chromic acid in acetic acid is added dropwise. The mixture is stirred for 2 hours and allowed to stand overnight. A few drops of methanol are added, the mixture is poured into ice water and neutralized with sodium carbonate. The mixture is extracted with ether. The ether extract is dried over magnesium sulfate, filtered and evaporated yielding an oil which solidifies. This solid is dissolved in ether, alcoholic HCl is added and the mixture is filtered. The solid is slurried in acetone, filtered and recrystallized twice from ethanol, m.p. 178°-178.5°C.

Workup

  1. waitto stand overnight
  2. extractionThe mixture is extracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customyielding an oil which
  8. filtrationthe mixture is filtered
  9. filtrationfiltered
  10. customrecrystallized twice from ethanol, m.p. 178°-178.5°C.

Sources & evidence

ORD record
ord-51214780e0c348608aabb5a2db373293
Source dataset
uspto-grants-1976_06
Patent number
US03966748

Reaction notes

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