Water → [3-(2-Hydroxypropan-2-yl)phenyl]boronic acid
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9]CC.O1CCC[CH2:13]1.C([O:20][B:21](OC(C)C)[O:22]C(C)C)(C)C.[OH2:30]>>[OH:30][C:3]([C:2]1[CH:1]=[C:9]([B:21]([OH:22])[OH:20])[CH:8]=[CH:7][CH:6]=1)([CH3:13])[CH3:4]Participants
Procedure
In a nitrogen atmosphere, 33 mL of 1.66 M n-butyllithium/hexane solution was dropwise added to tetrahydrofuran (200 mL) solution of the obtained compound at −60° C. or lower, and stirred for 20 minutes. 11.08 mL of triisopropoxyborane was added to the reaction liquid, and stirred for 30 minutes. Water was added to the reaction liquid, washed with diethyl ether, and the resulting aqueous layer was made acidic with aqueous 10% phosphoric acid solution. This was extracted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting crystal was collected to obtain 3.13 g of the entitled compound as a white solid.
Workup
- stirringstirred for 30 minutes
- washwashed with diethyl ether
- extractionThis was extracted with ethyl acetate
- washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
- dry with materialdried with anhydrous magnesium sulfate
- customThe solvent was evaporated away under reduced pressure
- customthe resulting crystal was collected
Sources & evidence
- ORD record
- ord-171b54d7ac6e45988b9093459d1ceee9
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935708B2
Reaction notes
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