Ethanol → 2-Hydroxy-estradiol

HRID 1076271Notes

Reaction equation

HRID 1076271 reaction equation
C[O:2][C:3]1[C:4]([OH:22])=[CH:5][C:6]2[CH2:7][CH2:8][C@@H:9]3[C@@H:18]([C:19]=2[CH:20]=1)[CH2:17][CH2:16][C@@:14]1([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]1[OH:21].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)C>C(O)C.O>[CH3:15][C@:14]12[CH2:16][CH2:17][C@H:18]3[C@@H:9]([CH2:8][CH2:7][C:6]4[CH:5]=[C:4]([OH:22])[C:3]([OH:2])=[CH:20][C:19]=43)[C@@H:10]1[CH2:11][CH2:12][C@@H:13]2[OH:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 664142-MethoxyestradiolHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2473042-Hydroxy-estradiol

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

0.70 g. of 2-methoxy-1,3,5 (10)-estratriene-3,17β-diol is heated under reflux and nitrogen purging in 10 ml. of toluene with 18 ml. of diisobutylaluminum hydride (20% in toluene) for 22 hours. The reaction mixture is cooled to about 0° C. and then decomposed with 5 ml. of ethanol and then with 5 ml. of ethanol-water mixture (1:1). The mixture is further worked up as set forth in Example 3. After purification from methanol, 0.45 g. of 1,3,5(10)-estratriene-2,3,17β-triol is obtained; m.p. 181°-183° C.; ε286 = 3420.

Workup

  1. temperatureunder reflux
  2. customAfter purification from methanol, 0.45 g

Sources & evidence

ORD record
ord-599edfd6536d4f4dbe335cb904193391
Source dataset
uspto-grants-1976_05
Patent number
US03956348

Reaction notes

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