Acetic Acid → HCID 11796064, compound

HRID 369508Notes

Reaction equation

HRID 369508 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:26][C:27](=[O:29])[CH3:28])=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[O:22][C:23](=[O:25])[CH3:24])[CH3:2].C(O)(=[O:32])C>[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([O:3][C:4]1[C:5]([O:26][C:27](=[O:29])[CH3:28])=[CH:6][C:7]2[C:8](=[O:32])[CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[O:22][C:23](=[O:25])[CH3:24])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 10787175HCID 10787175, compound

Product 1

HCID 11796064HCID 11796064, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Conditions

Temperature
15 °C

Procedure

A solution of chromium trioxide (1.6 g, 16 mmol) in 90% glacial acetic acid (7.5 mL) was added dropwise at 15° C. to a solution of 2-ethoxy-3,17β-diacetyl derivative (5), (1.5 g, 3.7 mmol) in glacial acetic acid (12 mL). The resulting mixture was stirred at 15° C. for 35 min. The mixiure was poured onto ice-water mixture (150 mL) and compound was extracted into ethyl acetate (3×180 mL). The combined organic layer was washed with water (100 mL), NaHCO3 solution (100 mL), water (100 mL), brine (100 mL), and dried over anhydrous sodium sulfate. The organic layer, upon evaporation under reduced pressure, provided a crude compound, which on purification on a silica gel column using hexane: ethyl acetate mixture aas eluant gave 1.20 g (55%) of estradiol (7): mp 195° C.; IR (KBr) 2980-2810, 1765, 1730, 1715, 1665, 1600, 1500, 918, 880 cm-1 ; 1H NMR (CDCl3) δ 0.89 (s, 3 H), 1.30-1.85 (m, 9 H), 1.90-2.45 (m, 11 H), 2.47-2.85 (m, 2 H), 4.15 (q, J=6.4 Hz, 2 H), 4.78 (t, J=8.5 Hz, 1 H), 6.95 (s, 1 H), 7.77 (s, 1 H). Anal. (C24H30O6) C, H.

Workup

  1. additionThe mixiure was poured onto ice-water mixture (150 mL) and compound
  2. extractionwas extracted into ethyl acetate (3×180 mL)
  3. washThe combined organic layer was washed with water (100 mL), NaHCO3 solution (100 mL), water (100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic layer, upon evaporation under reduced pressure
  6. customprovided a crude compound, which
  7. customon purification on a silica gel column

Sources & evidence

ORD record
ord-2af1f16a34dd4597abd0e76ec360a9e3
Source dataset
uspto-grants-2000_10
Patent number
US06136992

Reaction notes

Loading…