Methyl 4-methoxy-3-[(2-oxocyclopentyl)oxy]benzoate → HCID 23296053, compound

HRID 1954038Notes

Reaction equation

[CH2:1]([Li])CCC.[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[O:18][CH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC>[CH2:1]=[C:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[O:18][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[O:7][CH3:6])[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: -40 °C

Procedure

28.5 g of methyltriphenylphosphonium bromide are suspended under nitrogen in 300 ml of anhydrous THF and the mixture is cooled to -40° C. 50 ml of n-butyllithium (1.6M) in n-hexane are then added dropwise with stirring. After stirring at -20° to -10° for 30 min, a solution of 20 g of methyl 4-methoxy-3-(2-oxocyclopentyloxy)benzoate in 100 ml of abs. THF is added dropwise. The mixture is then allowed to warm to RT and is stirred for a further 1 h. It is poured onto water and extracted with ethyl acetate. The oil which remains after concentrating the organic phase is chromatographed on a silica gel column using ethyl acetate/petroleum ether (4:6). The chromatographically pure fractions are combined, concentrated and dried in a high vacuum. 12.7 g of the title compound are obtained as a colorless oil.

Workup

stirringAfter stirring at -20° to -10° for 30 min
temperatureto warm to RT
stirringis stirred for a further 1 h
additionIt is poured onto water
extractionextracted with ethyl acetate
concentrationafter concentrating the organic phase
customis chromatographed on a silica gel column
concentrationconcentrated
customdried in a high vacuum

Sources & evidence

ORD record: ord-5854a99894594048a45004d573f44c88
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121274

Reaction notes

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