Potassium Carbonate → 4,4,5,5-Tetramethyl-2-[4-(oxan-4-yloxy)phenyl]-1,3,2-dioxaborolane

HRID 2194586Notes

Reaction equation

HRID 2194586 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.CC1C=CC(S(O[CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:11][CH:10]=2)[O:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate

Product 1

HCID 711080474,4,5,5-Tetramethyl-2-[4-(oxan-4-yloxy)phenyl]-1,3,2-dioxaborolaneYield 24.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1 g, 4.5 mmole), tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate (1.4 g, 5.4 mmole) and K2CO3 (1.3 g, 9 mmole) in DMF (10 mL) was heated at 85° C. for 20 h. The mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by ISCO (silica gel, elute: 10% ethyl acetate in hexane) to give the title compound (335 mg, 24% yield) as a solid. MS (ESI) m/z: Calc. 304.2 (M+). Found: 305.3 (M++1).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by ISCO (silica gel, elute: 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ed8963968f8843f1a5704ca5aef864f3
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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