Oxalic Acid → HCID 15307267, compound

HRID 850847Notes

Reaction equation

HRID 850847 reaction equation
[F:1][C:2]([F:28])=[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][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@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][CH2:10]3

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 1530850217-Difluoromethylene-3-tetrahydropyranyloxy-8alpha-estra-1,3,5(10)-triene

Product 1

HCID 15307267HCID 15307267, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 1.2 g of 17-difluoromethylene-3-tetrahydropyranyloxy-8α-estra-1,3,5(10)-triene in 25 ml of methanol and 2.5 ml of water is refluxed with 1.2 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 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/ethyl acetate. 0.9 g of 17-difluoromethylene-8α-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/ethyl acetate

Sources & evidence

ORD record
ord-45c54bb1e32d47538181c6d1e3f0c568
Source dataset
uspto-grants-2000_01
Patent number
US06018062

Reaction notes

Loading…