Potassium Carbonate → HCID 86755356, compound

HRID 1005567Notes

Reaction equation

HRID 1005567 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].O[C:8]1[C:9](OCC2C=CC=CC=2)=[CH:10][C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:23]([C:24]=2[CH:25]=1)[CH2:22][CH2:21][C@@:19]1([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]1[O:26][CH2:27]C1C=CC=CC=1.[C:42]([CH2:46]I)(F)(F)F>CN(C=O)C>[CH2:1]([O:4][CH:18]([O:26][CH2:27][C:42]1[CH:46]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@:19]12[CH2:21][CH2:22][C@H:23]3[C@@H:14]([CH2:13][CH2:12][C:11]4[CH:10]=[CH:9][CH:8]=[CH:25][C:24]=43)[C@@H:15]1[CH2:16][CH2:17][CH2:20]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 677091,1,1-Trifluoro-2-iodoethane2×HCID 10412350HCID 10412350, compound

Product 1

HCID 86755356HCID 86755356, compoundYield 233.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Powdered K2CO3 (1.5 g, 11 mmol) was added to a solution of estradiol (6) (4.0 g, 8.5 mmol) in anhydrous DMF (50 mL) followed by dropwise addition of CF3CH2I (5.0 mL, 51 mmol) at room temperature. The resulting reaction mixture was heated at 110° C. for 3 h. Additional K2CO3 (2.5 g) and CF3CH2I (6 mL) were added, and the mixture was heated again at 130° C. for 2 h. The mixture was cooled in an ice bath and poured onto ice cold 3N HCl (125 mL). The aqueous layer was extracted with ether (2×200 mL). The combined ether layer was washed with 3 N HCl (100 mL), water (100 mL), brine (100 mL), and dried over anhydrous MgSO4. The ether layer was evaporated under reduced pressure and the resulting crude product on purification on a silica gel column gave estradiol (7) (4.5 g, 95%) as a colorless oil: IR (neat) 2910, 2850, 1600, 1500, 730, 690 cm-1 ; 1H NMR (CDCl3) δ 0.9 (s, 3 H), 1.1-2.4 (m, 13 H), 2.65-2.85 (m, 2 H), 3.50 (t, J=8.5 Hz, 1H), 4.40 (q, J=8.5 Hz, 2 H), 4.56 (s, 2 H), 5.05 (s, 2 H), 6.70 (s, 1 H), 6.98 (s, 1 H), 7.2-7.55 (m, 10 H). Anal. (C34H37F3O3) C, H.

Workup

  1. customThe resulting reaction mixture
  2. temperaturethe mixture was heated again at 130° C. for 2 h
  3. temperatureThe mixture was cooled in an ice bath
  4. additionpoured onto ice cold 3N HCl (125 mL)
  5. extractionThe aqueous layer was extracted with ether (2×200 mL)
  6. washThe combined ether layer was washed with 3 N HCl (100 mL), water (100 mL), brine (100 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. customThe ether layer was evaporated under reduced pressure
  9. customthe resulting crude product on purification on a silica gel column

Sources & evidence

ORD record
ord-506c0f869955422bab2a8d8648d00625
Source dataset
uspto-grants-2000_04
Patent number
US06054598

Reaction notes

Loading…