Trimethyl borate → HCID 58223487, compound

HRID 41247Notes

Reaction equation

HRID 41247 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH2:10][O:11][CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[O:15][CH3:16].C([Li])CCC.[B:22](OC)([O:25]C)[O:23]C.[Cl-].[NH4+]>O1CCCC1>[CH:12]([O:11][CH2:10][C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([B:22]([OH:25])[OH:23])=[C:3]([O:15][CH3:16])[CH:4]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 582234542-Bromo-5-(isopropoxymethyl)-1,3-dimethoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 58223487HCID 58223487, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (20 ml) solution of 2-bromo-5-(isopropoxymethyl)-1,3-dimethoxybenzene (1.85 g, 6.40 mmol) was added dropwise 2.77M n-butyllithium (2.77 ml, 7.68 mmol) at −78° C., and the mixture was stirred for one hour. To the mixture was added trimethyl borate (0.86 ml, 7.68 mmol), and the mixture was warmed to room temperature. After the reaction was completed, a saturated aqueous solution of ammonium chloride was added while cooling on ice, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1 then 1/1) to obtain the title compound (571 mg, 2.25 mmol).

Workup

  1. temperaturewhile cooling on ice, which
  2. extractionwas extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-9b27568306d84a02850008dd80e8a297
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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