Diethyl Ether → 17-hydroxy-3-methoxy-14,15-methylenestra-1,3,5(a)-trien

HRID 224239Notes

Reaction equation

HRID 224239 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C:12](=[O:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.CCOCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C@@H:12]([OH:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1.[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C@H:12]([OH:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 11130234HCID 11130234, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 17323317-hydroxy-3-methoxy-14,15-methylenestra-1,3,5(a)-trienHCID 11022909HCID 11022909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5-(10)-triene-17-one dissolved in 12 ml of absolute tetrahydrofuran are mixed with 100 mg of lithium aluminum hydride at 0° C. and set aside for 1.5 hours at room temperature. After adding ethyl acetate and ether the product is washed with saturated aqueous ammonium chloride solution and water, and the organic layer is separated, followed by drying with sodium sulphate and evaporating under vacuum. After preparative layer chromatography on silica gel (mobile phase: benzene/acetone/methanol 45:5:1) the residue yields 60 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17α-ol and 26 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17β-ol.

Workup

  1. washis washed with saturated aqueous ammonium chloride solution and water
  2. customthe organic layer is separated
  3. dry with materialby drying with sodium sulphate
  4. customevaporating under vacuum

Sources & evidence

ORD record
ord-0ecc57ca3cf64724bb41d7d0a44a0390
Source dataset
uspto-grants-1980_11
Patent number
US04231946

Reaction notes

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