Water → 1,3-Dimethoxy-17beta-hydroxyestra-1,3,5(10)-triene

HRID 839748Notes

Reaction equation

HRID 839748 reaction equation
[CH3:1][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](=[O:21])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].O>O1CCCC1>[CH3:1][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@@H:14]([OH:21])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 537114841,3-Dimethoxyestra-1,3,5(10)-trien-17-one

Product 1

HCID 706144001,3-Dimethoxy-17beta-hydroxyestra-1,3,5(10)-triene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-dimethoxyestra-1,3,5(10)-trien-17-one (2.0 g, 6.4 mM) in 10 ml of anhydrous tetrahydrofuran is added dropwise to a well-stirred suspension of lithium tri-t-butoxyaluminum hydride (4.86 g, 19 mM) in 40 ml of anhydrous tetrahydrofuran at 0°. The suspension is maintained at 0° for 1 hr, warmed to 40° for 1/2 hr, cooled to room temperature and poured into 200 ml of cold H2O. The basic aqueous solution is extracted with 3 × 50 ml of ether and 3 × 50 ml of methylene chloride. The combined organic extracts are washed with H2O, dried over Na2SO4 and evaporated in vacuo to give an oily residue which is chromatographed on 100 g of neutral silica gel. Elution with chloroform gives 1,3-dimethoxy-17β-hydroxyestra-1,3,5(10)-triene, yield 1.9 g (95%); m.p. 53°-55° (hexane).

Workup

  1. temperatureThe suspension is maintained at 0° for 1 hr
  2. temperaturewarmed to 40° for 1/2 hr
  3. extractionThe basic aqueous solution is extracted with 3 × 50 ml of ether and 3 × 50 ml of methylene chloride
  4. washThe combined organic extracts are washed with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customto give an oily residue which
  8. customis chromatographed on 100 g of neutral silica gel
  9. washElution with chloroform

Sources & evidence

ORD record
ord-6ef8e49506904464bcc9fcd891eb2889
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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