Water → [3-(2-Hydroxy-2-methylpropyl)phenyl]boronic acid

HRID 545244Notes

Reaction equation

HRID 545244 reaction equation
[CH2:1]([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].O1CCCC1.C([O:20][B:21]([CH:26]([CH3:28])[CH3:27])[O:22]C(C)C)(C)C.[OH2:29]>>[OH:29][C:7]([CH3:1])([CH3:6])[CH2:8][C:9]1[CH:27]=[C:26]([B:21]([OH:22])[OH:20])[CH:28]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 13583183IsopropyldiisopropoxyboraneHCID 178418244HCID 178418244, compound

Product 1

HCID 67171669[3-(2-Hydroxy-2-methylpropyl)phenyl]boronic acid

Procedure

In a nitrogen atmosphere at −78° C., 5.5 mL of 1.58 M n-butyllithium/hexane solution was dropwise added to tetrahydrofuran (50 mL) solution of 870 mg of the alcohols obtained in the above 4, then 925 mg of triisopropylboronic acid was dropwise added thereto, and stirred for 20 minutes. Water was added to the reaction solution, and washed with diethyl ether. The aqueous layer was made weakly acidic with 10% phosphoric acid, and then extracted with ethyl acetate. The organic layer was washed with water and saturated saline water in that order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain 274 mg of the entitled compound. Not purified, this was used in the next reaction.

Workup

  1. customobtained in the above 4
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated saline water in that order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-dda9117f1dc44ba4a4d79ab1356ff95b
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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