Hydrochloric Acid → (Z)-4-(1-(4-hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-en-2-yl)cyclohexanone

HRID 626183Notes

Reaction equation

HRID 626183 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[C:13](\[CH:16]2[CH2:25][CH2:24][C:19]3(OCC[O:20]3)[CH2:18][CH2:17]2)/[CH2:14][CH3:15])=[CH:8][CH:7]=1.Cl.O.C([O-])(O)=O.[Na+]>CO>[OH:32][C:29]1[CH:28]=[CH:27][C:26](/[C:12](/[C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][NH:2][CH3:1])=[CH:7][CH:8]=2)=[C:13](/[CH:16]2[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]2)\[CH2:14][CH3:15])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 89657384(Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-(1,4-dioxaspiro-[4.5]decan-8-yl)but-1-enyl)phenol

Product 1

HCID 71617374(Z)-4-(1-(4-hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-en-2-yl)cyclohexanoneYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-(1,4-dioxaspiro[4.5]decan-8-yl)but-1-enyl)phenol (90 mg) in MeOH (10 mL) was added aqueous of HCl (3 M, 1.5 mL), the mixture was stirred at room temperature for 2 hours, 20 mL water was added, pH was adjusted to 7-8 by addition of aqueous NaHCO3, and the mixture was extracted with ethyl acetate. The extract was dried, concentrated, and purified by column chromatography (CH2Cl2:MeOH=150:1) to give the desired product (22 mg, 27.5% yield). m/z=394[M+1]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated
  4. custompurified by column chromatography (CH2Cl2:MeOH=150:1)

Sources & evidence

ORD record
ord-178a3db5ea2848908596d8d037c94bed
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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