Lithium Hydroxide → 4-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid

HRID 736516Notes

Reaction equation

C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:28][CH3:29])([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:15]([CH3:27])[CH:14]=2)[CH2:11][CH3:12])=[CH:6][C:5]=1[CH3:30].[OH-].[Li+]>O1CCOCC1.O>[CH2:11]([C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[C:5]([CH3:30])[CH:6]=1)([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]2([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:15]([CH3:27])[CH:14]=1)[CH2:28][CH3:29])[CH3:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To an ambient temperature solution of 4-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid methyl ester (2.40 g, 5.73 mmol) in dioxane/water (30/30 ml) is added lithium hydroxide (412 mg, 17.20 mmol) and heated to 60° C. for 1 h. The reaction is concentrated and partitioned between Et2O/EtOAc (150/150 ml) and 1N HCl (50 ml). The aqueous phase is extracted with a second portion of EtOAc (100 ml) and the combined organic phases are washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated to yield the title compound (1.57 g, 68%).

Workup

concentrationThe reaction is concentrated
custompartitioned between Et2O/EtOAc (150/150 ml) and 1N HCl (50 ml)
extractionThe aqueous phase is extracted with a second portion of EtOAc (100 ml)
washthe combined organic phases are washed with water (50 ml), brine (50 ml)
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-35c9b9f760e1406b9fcde8577c527d16
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595345B2

Reaction notes

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