Lithium Hydroxide → DCP-LA

HRID 2376794Notes

Reaction equation

C[O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:13][CH:12]1[CH2:14][CH:15]1[CH2:17][CH:16]1[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[OH-].[Li+].O1CCOCC1.[Cl-].[NH4+]>C(OCC)(=O)C>[CH2:18]([CH:16]1[CH2:17][CH:15]1[CH2:14][CH:12]1[CH2:13][CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:23])=[O:2])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid methyl ester (4.89 g), 1N aqueous solution (33.4 ml) of lithium hydroxide and dioxane (33 ml) was stirred at 60° C. overnight. The mixture was poured into a mixture of ethyl acetate (EA) and a saturated aqueous solution of ammonium chloride. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified by chromatography on silica gel (eluted with 20% EA in n-hexane). The fractions including 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid were collected and concentrated in vacuo to give 8-(2-((2-pentylcyclopropan-1-yl)methyl)cyclopropyl)octanoic acid (4.01 g) as an oil.

Workup

washThe separated organic layer was washed with water
dry with materialdried over magnesium sulfate
filtrationAfter filtration
concentrationthe filtrate was concentrated in vacuo
customThe obtained residue was purified by chromatography on silica gel (eluted with 20% EA in n-hexane)
customwere collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f9d91d64a8894ab38fe3be65100f46b0
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468389B2

Reaction notes

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