HCID 58675134, compound → 3-Hydroxy-5-(4-iodo-phenyl)-pentanoic acid

HRID 1297261Notes

Reaction equation

HRID 1297261 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][CH:8]([OH:18])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(C)(C)C>C1(C)C=CC=CC=1>[OH:18][CH:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)[CH2:7][C:6]([OH:19])=[O:5]

Participants

3

Reactant 1

HCID 58675134HCID 58675134, compound2×

Product 1

HCID 586751313-Hydroxy-5-(4-iodo-phenyl)-pentanoic acidYield 57.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Silica gel (19 g) was added to a stirred solution of 3-hydroxy-5-(4-iodo-phenyl)-pentanoic acid tert-butyl ester (Intermediate 9, 1.2 g, 3.2 mmol) in toluene (100 mL) and the resulting suspension heated at reflux for 5.5 hours. The reaction was cooled to room temperature and then filtered through a thin pad of celite, washing with 20% methanol/dichloromethane (2×50 mL). The filtrate was evaporated under reduced pressure to give the title compound (586mg, 57%) as a white solid. LC/MS: 3.01 min; z/e 319, calcd (M−1) 319. 1H NMR (400 MHz: DMSO-d6): 7.63 (2 H), 7.00 (2 H), 3.77 (1 H), 2.60 (2 H), 2.3 (2 H), 1.62 (2 H).

Workup

  1. temperaturethe resulting suspension heated
  2. temperatureat reflux for 5.5 hours
  3. filtrationfiltered through a thin pad of celite
  4. washwashing with 20% methanol/dichloromethane (2×50 mL)
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ebae115cc53743599576263bbe838a75
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

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