Ethyl acetate hexane → HCID 178455821, compound

HRID 1490143Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[N+](=CP(=O)([O-])OC)=[N-].[CH3:15][O:16][C:17]1[CH:29]=[CH:28][C:20]([O:21][C@H:22]2[CH2:25][C@H:24]([CH:26]=O)[CH2:23]2)=[CH:19][CH:18]=1.CCCCCC.C(OCC)(=O)C>C1COCC1>[CH3:15][O:16][C:17]1[CH:29]=[CH:28][C:20]([O:21][C@H:22]2[CH2:25][C@H:24]([C:26]#[CH:1])[CH2:23]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A slurry of potassium tert-butoxide (7.85 g, 70 mmol) in THF (50 ml) was cooled to -78° C. under argon atmosphere. To this was added a solution of methyl (diazomethyl)phosphonate (J. Org. Chem. 1979, 44, 4997) (12.5 g, 70 mmol) in THF (100 ml), followed after 0.5 h by a solution of trans-3-(4-methoxyphenoxy)cyclobutanecarbaldehyde (12.1 g, 58.7 mmol) in THF (100 ml) at the same temperature. The resulting solution was stirred at -78° C. for 3 h and then maintained at room temperature for another 8 h. The reaction was quenched with water (300 ml) and the aqueous mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine (200 ml), dried (MgSO4) and concentrated in vacuo to give yellow solids. Silica-gel column chromatography of the solids {SiO2, 800 g; hexane/ethyl acetate (9/1)} of the solids afforded 6.49 g (55%) of {trans-3-(4-methoxyphenoxy)cyclobutyl }ethyne as white solids: 1H NMR δ6.84-6.70 (m, 4H), 4.92-4.82 (m, 1H), 3.76 (s, 3H), 3.20-3.03 (m, 1H), 2.64-2.40 (m, 4H), 2.19 (s, 1H).

Workup

temperaturemaintained at room temperature for another 8 h
customThe reaction was quenched with water (300 ml)
extractionthe aqueous mixture was extracted with ethyl acetate
washThe combined organic extracts were washed with brine (200 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto give yellow solids

Sources & evidence

ORD record: ord-66fd62ba22d644d3ac38a4d502294899
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681858

Reaction notes

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