Oxalic Acid → 17-Difluoromethylene-estra-1,3,5(10)-trien-3-ol

HRID 369040Notes

Reaction equation

HRID 369040 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 18397081HCID 18397081, compound

Product 1

HCID 992649817-Difluoromethylene-estra-1,3,5(10)-trien-3-olYield 47.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1.3 g of crude 17-difluoromethylene-3-(tetrahydro-pyran-2-yl-oxy)-estra-1,3,5(10)-triene in 30 ml of methanol and 3 ml of water are suspended with 1.3 g of oxalic acid for 1 hour at a bath temperature of 100° C. Then, it is added to water, extracted three times with dichloromethane, washed neutral, dried on sodium sulfate and evaporated to dryness in a vacuum. 1.0 g of crude 17-difluoromethylene-estra-1,3,5(10)-trien-3-ol, which is chromatographed on silica gel with hexane/ethyl acetate, is obtained. 480 mg of pure 17-difluoromethylene-estra-1,3,5(10)-trien-3-ol is obtained as colorless crystals with a melting point of 154-156° C.

Workup

  1. customtemperature of 100° C
  2. extractionextracted three times with dichloromethane
  3. washwashed neutral
  4. customdried on sodium sulfate
  5. customevaporated to dryness in a vacuum
  6. custom1.0 g of crude 17-difluoromethylene-estra-1,3,5(10)-trien-3-ol, which is chromatographed on silica gel with hexane/ethyl acetate
  7. customis obtained

Sources & evidence

ORD record
ord-b47fe7cec032458c99f8edeff64f7759
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

Loading…