HCID 21225731, compound → HCID 22789973, compound

HRID 1076272Notes

Reaction equation

HRID 1076272 reaction equation
C[O:2][C:3]1[C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14]3(OCC[O:21]3)[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[C:6]([CH3:25])=[CH:5][CH:4]=1.[H-].C([Al+]CC)C>C1(C)C=CC=CC=1>[CH3:25][C:6]1[C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[C:3]([OH:2])=[CH:4][CH:5]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[OH:21]

Participants

4

Reactant 2

HCID 21225731HCID 21225731, compoundHCID 22789964HCID 22789964, compound

Product 1

HCID 22789973HCID 22789973, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.0 g. of 1-methoxy-17,17-ethylenedioxy-4-methyl-1,3,5(10)-estratriene is heated for 24 hours under reflux and nitrogen purging in 20 ml. of toluene with 25 ml. of diethylaluminum hydride (20% in toluene). The reaction mixture is decomposed and worked up as described in Example 3. The dried residue is extracted with a methylene chloride-methanol mixture (1:1), concentrated to dryness under vacuum, and crystallized from hexane. After recrystallization from methylene chloride-isopropyl ether with carbon, 1.57 g. of 4-methyl-1,3,5(10)-estratriene-1,17β-diol, m.p. 226°-229° C., is obtained. [α]D = +177.9° (dioxane); ε280 = 1930.

Workup

  1. temperatureunder reflux
  2. extractionThe dried residue is extracted with a methylene chloride-methanol mixture (1:1)
  3. concentrationconcentrated to dryness under vacuum
  4. customcrystallized from hexane
  5. customAfter recrystallization from methylene chloride-isopropyl ether with carbon, 1.57 g

Sources & evidence

ORD record
ord-726f1b2077ba4840ac2106c1a3d8de5d
Source dataset
uspto-grants-1976_05
Patent number
US03956348

Reaction notes

Loading…