Trioxifene → [2-(4-Methoxyphenyl)-3,4-dihydronaphth-1-yl][4-(1-pyrrolidinyl-2-ethoxy)phenyl]carbinol

HRID 399443

Reaction equation

HRID 399443 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[O:20])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)[OH:20])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 50139TrioxifeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 10182739[2-(4-Methoxyphenyl)-3,4-dihydronaphth-1-yl][4-(1-pyrrolidinyl-2-ethoxy)phenyl]carbinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

850 mg (1.9 mmol) of [2-(4-methoxyphenyl)-3,4-dihydronaphth-1-yl][4-(1-pyrrolidinyl-2-ethoxy)phenyl] methanone was dissolved in 100 mL of THF and 160 mg (4 mmol) of LiAlH4 was added. The reaction mixture was stirred at room temperature and under a N2 atmosphere for eighteen hours. The reaction mixture was evaporated to dryness in vacuo. Fifty mL of water was carefully added to the residue and the reaction mixture was extracted twice with 100 mL of EtOAc. The EtOAc extracts were combind and washed with water, then the EtOAc layer was removed and dried by filteration through anhydrous Na2SO4 and evaporated to dryness in vacuo. This yielded 670 mg of the title compound as a white amorphous powder.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. additionFifty mL of water was carefully added to the residue
  3. extractionthe reaction mixture was extracted twice with 100 mL of EtOAc
  4. washwashed with water
  5. customthe EtOAc layer was removed
  6. dry with materialdried by filteration through anhydrous Na2SO4
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-0c6825c12e8446f98cbbe66ea9902b83
Source dataset
uspto-grants-1998_10
Patent number
US05821253

Linked notes

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