Hydrochloric Acid → HCID 69098014, compound

HRID 1503078Notes

Reaction equation

[CH2:1]1[C:3]2([CH2:8][C:7](=[O:9])[O:6][C:5](=[O:10])[CH2:4]2)[CH2:2]1.[CH3:11][Mg]Br.CC1CCCO1.Cl>O1CCCC1.[Cu]Cl.C(OC)(C)(C)C.O>[O:9]=[C:7]([CH3:11])[CH2:8][C:3]1([CH2:4][C:5]([OH:6])=[O:10])[CH2:2][CH2:1]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 4.4 g 6-oxa-spiro[2.5]octane-5,7-dione (31 mmole) in 66 ml tetrahydrofuran are added 600 mg copper(I)chloride (6 mmole, 0.2 eq). The mixture is cooled to −20° C. and 9.8 ml of methylmagnesium bromide in 2-methyl tetrahydrofuran (3.2 M solution in 2-methyl tetrahydrofuran, 31 mmole, 1.0 eq) are added dropwise over 0.5 hours. The mixture is warmed to room temperature and stirred for 2 hours. 66 ml of water are added and the mixture is acidified to pH 3.0 by addition of 20.4 g of 2 M hydrochloric acid. 50 ml of methyl tert-butyl ether are added and the phases are separated. The aqueous phase is extracted again with 50 ml of methyl tert-butyl ether and the combined organic phases are washed with 20 ml of brine and concentrated to dryness. The resulting crude product is directly used in the next step (esterification to [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester).

Workup

temperatureThe mixture is warmed to room temperature
customthe phases are separated
extractionThe aqueous phase is extracted again with 50 ml of methyl tert-butyl ether
washthe combined organic phases are washed with 20 ml of brine
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-a0347d69968a45ba977e482e3d6ea224
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212120B2

Reaction notes

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