Methyl iodide → HCID 58120020, compound

HRID 456213Notes

Reaction equation

HRID 456213 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([B:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]2)[CH:7]=1)[CH3:2].IC.[CH3:26][Si](C)(C)N[Si](C)(C)C.[Na]>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([B:14]2[O:15][C:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[O:18]2)[CH:7]=1)[CH3:26])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 45051731Sodium hexamethyidisilazaneHCID 58120060[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester

Product 1

HCID 58120020HCID 58120020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (0.100 g, 0.31 mmol) and iodomethane (0.04 mL, 0.63 mmol) in THF (5 mL) at −78° C. was added sodium hexamethyldisilazane (1M in THF; 0.63 mL, 0.63 mmol). The reaction was warmed to room temperature and stirred under N2 for 1 hour, and then quenched with H2O and partitioned between EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customquenched with H2O
  2. custompartitioned between EtOAc and H2O
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e05d10193b844a1fac68dfb408fdc7be
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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