Oxalic Acid → HCID 15307279, compound

HRID 369055Notes

Reaction equation

HRID 369055 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(1l)-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° (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-dbc3870bffe74fecb397914084658f50
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

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