Water → HCID 57672511, compound

HRID 2101801Notes

Reaction equation

HRID 2101801 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 57672454HCID 57672454, compoundHCID 57672511HCID 57672511, compoundYield 179.3%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 25.1 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 25.1 (0.063 g, 0.3 mmol) in EtOAc (3 mL) at 23° C. was added quinoline (0.06 mL, 0.5 mmol), followed by Lindlar Catalyst (0.003 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 then the mixture was extracted with EtOAc. After concentration, the residue was purified on silica gel (0%-20% EtOAc/hexane) to give (S,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate 35.1 (0.063 g, 99%). MS ESI (pos.) m/e: 235.1 (M+H)+.

Workup

  1. customat 23° C.
  2. extractionthe mixture was extracted with EtOAc
  3. concentrationAfter concentration
  4. customthe residue was purified on silica gel (0%-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-212063e41a6e4dca9f30ee5f0b51405d
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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