HCID 53758475, compound → 4-Hydroxytoremifene

HRID 2396137Notes

Reaction equation

HRID 2396137 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[CH:20][CH:19]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1>C(O)C.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:1][CH2:2][CH2:3]/[C:4](/[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[C:5](\[C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)/[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 53758475HCID 53758475, compound

Product 1

HCID 30351984-Hydroxytoremifene

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

8.4 g of 4-chloro-1-(4-benzyloxyphenyl)-1-[4-[2-(N,N-dimethylamino )-ethoxy]phenyl]-2-phenyl-1-butene is hydrogenated in 340 ml of ethanol-ethyl acetate (1: 1) containing 11 drops of triethylamine using 5%Pd--C as a catalyst. The catalyst is filtered off and the solvent is evaporated. The residue is treated with ethanol and the product is filtered. The yield is 4.9 g (71%).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated
  3. additionThe residue is treated with ethanol
  4. filtrationthe product is filtered

Sources & evidence

ORD record
ord-19c5d8208b8f4c9fa4eb87f8a76e3eac
Source dataset
uspto-grants-1996_02
Patent number
US05491173

Reaction notes

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