Oxalic Acid → HCID 15307279, compound

HRID 850839Notes

Reaction equation

HRID 850839 reaction equation
[F:1][C:2]([F:28])=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C:18](=[CH:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH:16]=[CH:15][C:14]([O:21]C2CCCCO2)=[CH:13][C:12]=1[CH2:11][CH2:10]3.C(O)(=O)C(O)=O>CO.O>[F:1][C:2]([F:28])=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C:18](=[CH:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH:16]=[CH:15][C:14]([OH:21])=[CH:13][C:12]=1[CH2:11][CH2:10]3

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 15307278HCID 15307278, compound

Product 1

HCID 15307279HCID 15307279, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 900 mg of 17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10),9(11)-tetraene in 19 ml of methanol and 1.9 ml of water is refluxed with 900 mg of oxalic acid for 0.5 hour at a bath temperature of 100° C. Then, it is concentrated by evaporation in a vacuum diluted with ethyl acetate, washed three times with water, once with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. After crystallization from hexane, 0.5 g of 17-difluoromethylene-estra-1,3,5(10),9(11)-tetraen-3-ol is obtained as colorless crystals with a melting point of 134-135° C., [α]D22 =+89.6° (c=0.515% in pyridine).

Workup

  1. concentrationThen, it is concentrated by evaporation in a vacuum
  2. additiondiluted with ethyl acetate
  3. washwashed three times with water
  4. dry with materialonce with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customchromatographed on silica gel with hexane/ethyl acetate
  7. customAfter crystallization from hexane

Sources & evidence

ORD record
ord-2eed03f4878a4777bca41742af94ea93
Source dataset
uspto-grants-2000_01
Patent number
US06018062

Reaction notes

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