Water → HCID 21505643, compound

HRID 1287642Notes

Reaction equation

HRID 1287642 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH:18]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[OH:19])[CH2:13][CH:14]=3)[N:5]=2)[CH2:3][CH2:2]1.[Cr](O)(O)(=O)=O.O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.CO>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[O:19])[CH2:13][CH:14]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 24425Chromic AcidHCID 516892Sodium BicarbonateHCID 21505637HCID 21505637, compound

Product 1

HCID 21505643HCID 21505643, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 176Acetic AcidSolvent2×

Procedure

A 0.36 g. portion of 4-(5-cyclopropyl-1,2,4-oxadiazol- 3-yl)-3,6-dihydro-α-(p-fluorophenyl)-1(2H)-pyridinebutanol, prepared as described in Example 11, in 10 ml. of acetic acid is stirred at room temperature. A 6 ml. portion of chromic acid in acetic acid solution is added dropwise. The mixture is stirred for 2 hours and then allowed to stand overnight. A few drops of methanol and some water is added and the solution is neutralized with solid sodium bicarbonate. The mixture is extracted 3 times with ether. The extracts are dried over magnesium sulfate, filtered and evaporated, yielding a white solid which is recrystallized from aqueous methanol, m.p. 67°-68° C.

Workup

  1. waitto stand overnight
  2. extractionThe mixture is extracted 3 times with ether
  3. dry with materialThe extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customyielding a white solid which
  7. customis recrystallized from aqueous methanol, m.p. 67°-68° C.

Sources & evidence

ORD record
ord-3f817e1a23e44f22bdeb459505c0a34c
Source dataset
uspto-grants-1976_10
Patent number
US03985754

Reaction notes

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