Water → HCID 21505611, compound

HRID 1287641Notes

Reaction equation

HRID 1287641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[O:22][N:21]=[C:20]([CH3:23])[CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cr](O)(O)(=O)=O.C(=O)(O)[O-].[Na+].O>C(O)(=O)C.CO>[CH3:23][C:20]1[CH:19]=[C:18]([C:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:24])[CH2:13][CH:14]=2)[O:22][N:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24425Chromic AcidHCID 516892Sodium BicarbonateHCID 54283188HCID 54283188, compound

Product 1

HCID 21505611HCID 21505611, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 176Acetic AcidSolvent2×

Procedure

A 1.65 g. portion of 3,6-dihydro-α-(p-fluorophenyl)- 4-(3-methyl-5-isoxazolyl)-1(2H)-pyridine butanol, prepared as described in Example 10, in 35 ml. of acetic acid is stirred at room temperature. A 30 ml. portion of chromic acid in acetic acid (prepared by dissolving 1.1 gm. of chromium oxide in 50 ml. of acetic acid and 10 ml. of water) is added dropwise and the mixture is stirred for 3 hours and then allowed to stand overnight. A few drops of methanol are added and sufficient solid sodium bicarbonate to neutralize the solution. Water is also added. The mixture is extracted 3 times with ether. The extracts are dried over magnesium sulfate, filtered and evaporated yielding a pink solid which is recrystallized twice from methanol, m.p. 96°-98° 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 pink solid which
  7. customis recrystallized twice from methanol, m.p. 96°-98° C.

Sources & evidence

ORD record
ord-54928926231d4a959191b15d215ae6d0
Source dataset
uspto-grants-1976_10
Patent number
US03985754

Reaction notes

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