Oxalic Acid → HCID 15307284, compound

HRID 850844Notes

Reaction equation

HRID 850844 reaction equation
[F:1][C:2]([F:29])=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][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][C@@H:10]3[CH3:28].C(O)(=O)C(O)=O>CO.O>[F:1][C:2]([F:29])=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][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][C@@H:10]3[CH3:28]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 1839708317-Difluoromethylene-7beta-methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-triene

Product 1

HCID 15307284HCID 15307284, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 1.2 g of 17-difluoromethylene-7β-methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-triene in 25 ml of methanol and 2.5 ml of water is refluxed with 1.2 g of oxalic acid for 1 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-7β-methyl-estra-1,3,5(10)-trien-3-ol is obtained as colorless crystals with a melting point of 119-120° C., [α]D22 =-10.6° (c=0.5% 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-94219ef90f6e476eb93f55759b103e49
Source dataset
uspto-grants-2000_01
Patent number
US06018062

Reaction notes

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