Tetrahydro-4H-pyran-4-ol → (4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid ethyl ester

HRID 524389Notes

Reaction equation

[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[N+]=[N-])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>C(Cl)Cl>[CH2:17]([O:16][C:14](=[O:15])[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])=[CH:8][CH:9]=1)[O:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[CH3:18]

Participants

Conditions

Temperature: 25 °C

Procedure

Ethyl 2-(4-cyclopropylsulfonylphenyl)-2-diazo-acetate (36 g, 121.62 mmol) was dissolved in DCM (608 mL) under argon atmosphere. To this solution, 4-hydroxy tetrahydropyran (12.75 mL, 133.78 mmol) was added followed by rhodium(II)acetate dimer (1.12 g, 0.021 mmol). Mixture was stirred at 25° C. for 1 hr. Reaction mixture was diluted with DCM (500 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 product (4-cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid ethyl ester (50 g).

Workup

customReaction mixture
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-00258f0a47cc40dd80cb47d971b3cadf
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340506B2

Reaction notes

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