Potassium Carbonate → HCID 57586498, compound

HRID 1670152Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=O)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27]C)=[O:25])C.[C:30](=O)([O-])[O-].[K+].[K+].C/C(/[O-])=C(/P(OC)(OC)=O)\[N+]#N>CO>[CH3:1][O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:30])[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-[2-(2-ethoxycarbonyl-ethyl)-3-(6-oxo-hexyl)-phenoxy]-butyric acid ethyl ester (7.0 g, 17.24 mmol) was added a solution of potassium carbonate (7.14 g, 51.72 mmol) in MeOH (200 mL) and the resulting mixture was cooled to 0° C. Then the Ohira's reagent (ref. cited in Synlett, 1996, 521) (6.3 g, 32.8 mmol) in MeOH (50 mL) was added slowly. The cooling bath was removed upon the end of addition and the reaction mixture was stirred at room temperature for 5 hr. The reaction was then extracted into ethyl acetate and washed with brine. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified by column chromatography using 50% ethyl acetate-hexanes as eluant to give the title compound (4.6 g, 71%) as a light yellow oil.

Workup

customThe cooling bath was removed upon the end of addition
extractionThe reaction was then extracted into ethyl acetate
washwashed with brine
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude material was purified by column chromatography

Sources & evidence

ORD record: ord-ea39efaec0b74ec1a70f4149655b5af8
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989454B2

Reaction notes

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