Dichloromethane → HCID 89672892, compound

HRID 626123Notes

Reaction equation

CS([O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:27]2[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=2)=[O:26])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C>[OH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([O:5][CH:6]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]3)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate (0.6 g, 2.26 mmol), bis(4-hydroxyphenyl)methanone (2.15 g, 10.0 mmol) and K2CO3 (313 mg, 2.26 mmol) in 12 mL DMF was heated at 100° C. for 3.5 h, then quenched with water, and extracted with EtOAc. The extract was washed with water, dried, and concentrated to give a residue, to which was added CH2Cl2 and the white suspension thus formed removed and filtration. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (petroleum ether/CH2Cl2/acetone=4/2/1) to give the desired product (400 mg, 46% yield).

Workup

customquenched with water
extractionextracted with EtOAc
washThe extract was washed with water
customdried
concentrationconcentrated
customto give a residue
customthe white suspension thus formed
customremoved
filtrationfiltration
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography (petroleum ether/CH2Cl2/acetone=4/2/1)

Sources & evidence

ORD record: ord-b40d2a9f3ec8415a9f8686638a62463f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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