3-Furanol, tetrahydro- → (4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-furan-3-yloxy)]-acetic acid ethyl ester

HRID 1889174Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH:17]2[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)=[N+]=[N-])[CH3:2].[OH:21][CH:22]1[CH2:26][CH2:25][O:24][CH2:23]1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH:17]2[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[O:21][CH:22]1[CH2:26][CH2:25][O:24][CH2:23]1)[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

(4-Cyclopropanesulfonyl-phenyl)diazo acetic acid ethyl ester (2 gm, 6.74 mmol) was dissolved in DCM (33 mL) under argon atmosphere. To this solution, 3-hydroxy tetrahydrofuran (1.36 mL, 16.87 mmol) was added followed by rhodium(II)acetate dimer (62 mg, 0.14 mmol). Mixture was stirred at 25° C. for 3 hr. Reaction mixture was diluted with DCM (25 mL), organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a crude product which was purified by column chromatography using 35-40% ethyl acetate in hexane as eluent to provide (4-cyclopropanesulfonyl-phenyl)-[(tetrahydro-furan-3-yloxy)]-acetic acid ethyl ester (1 gm).

Workup

customReaction mixture
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a crude product which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-e394c98859a74091b87c386d827547d1
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501955B2

Reaction notes

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