Methyl iodide → HCID 67365258, compound

HRID 245712Notes

Reaction equation

HRID 245712 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:24])[O:20][CH:21]([CH3:23])[CH3:22].[H-].[Na+].I[CH3:28].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:14])([CH3:15])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:4]=1[N:18]([CH3:28])[C:19](=[O:24])[O:20][CH:21]([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67363825Isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

Product 1

HCID 67365258HCID 67365258, compoundYield 134.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (0.298 mmol, 0.10 g) in tetrahydrofuran (1 ml) at room temperature were subsequently added sodium hydride (60% dispersion in mineral oil, 0.350 mmol, 0.014 g) and iodomethane (0.803 mmol, 0.05 ml). After 1 hour aqueous ammonium chloride solution was added and extracted with dichloromethane (three times). The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to yield isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl(methyl)carbamate (0.14 g) which was used without further purification.

Workup

  1. customat room temperature
  2. extractionextracted with dichloromethane (three times)
  3. dry with materialThe combined organic extracts were dried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae4c4da0567c4285976ecd7b83e12160
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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