Water → HCID 57672423, compound

HRID 2101799Notes

Reaction equation

HRID 2101799 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:14]#[C:15][CH2:16][CH3:17])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1.O>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([C:14]#[C:15][CH2:16][CH3:17])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1.[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8](/[CH:14]=[CH:15]\[CH2:16][CH3:17])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7047QuinolineHCID 57672454HCID 57672454, compound

Product 2

HCID 57672423HCID 57672423, compoundYield 207.7%HCID 57672454HCID 57672454, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-methyl 3-(4-hydroxyphenyl)hept-4-ynoate 24.1 was prepared by a method based on that reported in U.S. Patent Application Publication No. 2006/0004012 which is hereby incorporated by reference. To a stirred solution of 24.1 (0.077 g, 0.3 mmol) in EtOAc (3 mL) at 23° C. was added quinoline (0.08 mL, 0.7 mmol), followed by Lindlar Catalyst (0.004 g, 0.03 mmol). The reaction was placed under an atmosphere of hydrogen and then stirred at room temperature. After 15 hours, water was added to the mixture, and the mixture was extracted with EtOAc. After concentration, the residue was purified on silica gel (0%-20% EtOAc/hexane) to give (R,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate 34.1 (0.073 g, 94%). MS ESI (pos.) m/e: 235.1 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. concentrationAfter concentration
  3. customthe residue was purified on silica gel (0%-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-fe1bd79649a14ea6870aebedc82ddc77
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

Loading…