Ethanol → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-ol

HRID 30761

Reaction equation

HRID 30761 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:24])[C:8]([CH3:10])([CH3:9])[O:7][B:6]([C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][C:17](OCC)=[O:18])=[CH:13][CH:12]=2)[O:5]1.O1CCCC1.C(O)C>O>[CH3:9][C:8]1([CH3:10])[C:4]([CH3:3])([CH3:24])[O:5][B:6]([C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][CH2:17][OH:18])=[CH:13][CH:12]=2)[O:7]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 3464653Ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetateHCID 4311764Sodium borohydride

Product 1

HCID 231341922-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-olYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.33 g) was added to a mixture of ethyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-acetate (1.33 g), tetrahydrofuran (10 mL) and ethanol (10 mL). The mixture was stirred at room temperature for 4 hrs, and water was added. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to afford the title compound (1.13 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-bbf95566f52e4ad68e69211467a2c659
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Linked notes

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