Potassium Hydroxide → HCID 386752, compound

HRID 369509Notes

Reaction equation

HRID 369509 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6]1[C:7]([O:29]C(=O)C)=[CH:8][C:9]2[C:10](=[O:28])[CH2:11][C@@H:12]3[C@@H:21]([C:22]=2[CH:23]=1)[CH2:20][CH2:19][C@@:17]1([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]1[O:24]C(=O)C)[CH3:4]>CO>[CH2:3]([O:5][C:6]1[C:7]([OH:29])=[CH:8][C:9]2[C:10](=[O:28])[CH2:11][C@@H:12]3[C@@H:21]([C:22]=2[CH:23]=1)[CH2:20][CH2:19][C@@:17]1([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]1[OH:24])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11796064HCID 11796064, compound

Product 1

HCID 386752HCID 386752, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 20% solution of KOH in methanol (5 mL) was added drcpwise to a suspension of estradiol (7) (0.95 g, 2.3 mmol) in anhydrous methanol (12 mL). The resulting reaction mixture was stirred at room temperature for 4 h. The solvent was removed under reduced pressure at 42-45° C. The residue was diluted with ice-water mixture (30 mL), and extracted with ethyl acetate (3×125 mL). The combined organic layer was washed with ice-cold water (30 mL), brine (30 mL) and dried over anhydrous sodium sulfite. The organic layer, on evaporation under vacuum, gave estradiol (10) (0.7 g, 92%). An analytical sample was prepared by a short column chromatography on silica gel using EtOAc, followed by EtOAc--MeOH (18:1), and finally chloroform: mp 194-196° C.; IR (KBr) 3400-3200, 2960-2842, 1650, 1590, 1500, 890, 852 cm-1 ; 1H NMR (DMSO-d6 +D2O) δ 0.85 (s, 3 H), 1.20-1.80 (m, 10 H), 1.82-2.82 (m, 8 H), 3.72 (t, J=8.5 Hz, 1 H), 4.20 (q, J=6.4 Hz, 2 H), 6.85 (s, 1 H), 7.58 (s, 1 H). Anal. (C20H26O4) C, H.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed under reduced pressure at 42-45° C
  3. additionThe residue was diluted with ice-water mixture (30 mL)
  4. extractionextracted with ethyl acetate (3×125 mL)
  5. washThe combined organic layer was washed with ice-cold water (30 mL), brine (30 mL)
  6. dry with materialdried over anhydrous sodium sulfite
  7. customThe organic layer, on evaporation under vacuum

Sources & evidence

ORD record
ord-f92f197b75f748d48c0893acefdb59d3
Source dataset
uspto-grants-2000_10
Patent number
US06136992

Reaction notes

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