Oxalic Acid → HCID 15307269, compound

HRID 369046Notes

Reaction equation

HRID 369046 reaction equation
[F:1][C:2]([F:30])=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([C@@H:19]([O:21][CH3:22])[CH2:20][C@:4]12[CH3:5])[C:17]1[CH:16]=[CH:15][C:14]([O:23]C2CCCCO2)=[CH:13][C:12]=1[CH2:11][CH2:10]3.C(O)(=O)C(O)=O>CO.O>[F:1][C:2]([F:30])=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([C@@H:19]([O:21][CH3:22])[CH2:20][C@:4]12[CH3:5])[C:17]1[CH:16]=[CH:15][C:14]([OH:23])=[CH:13][C:12]=1[CH2:11][CH2:10]3

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 15307270HCID 15307270, compound

Product 1

HCID 15307269HCID 15307269, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 1.2 g of 17-difluoromethylene-11β-methoxy-3-tetrahydropyranyloxy-estra-1,3,5(10)-triene in 25 ml of methanol and 2.6 ml of water is refluxed with 1.2 g 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 with water, 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/acetone. After crystallization from hexane, 0.9 g of 17-difluoromethylene-11β-methoxy-estra-1,3,5(10)-trien-3-ol is obtained as colorless crystals with a melting point of 245-247° C., [α]D22 +77.3° (c=0.535% in pyridine).

Workup

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

Sources & evidence

ORD record
ord-2c3f5214f18f4b31b96767c2d97b1f45
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

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