Methyl iodide → Tert-butyl 2-propenyloxy(methyl)carbamate

HRID 43243Notes

Reaction equation

HRID 43243 reaction equation
[H-].[Na+].[CH2:3]([O:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:4]=[CH2:5].I[CH3:16]>O1CCCC1.O>[CH2:3]([O:6][N:7]([CH3:16])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22322878Carbamic acid, (2-propenyloxy)-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 59471294Tert-butyl 2-propenyloxy(methyl)carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Sodium hydride (NaH, 60% dispersion in mineral oil; 390 mg, 9.7 mmol, 1.1 equiv) was added to a stirred solution of tert-butyl 2-propenyloxycarbamate (2.0 g, 8.8 mmol, 1.0 equiv) in tetrahydrofuran (THF; 23 mL) at 0° C. The resulting bubbling white mixture was warmed to 23° C. and stirred for 15 minutes (min) Iodomethane (660 μL, 11 mmol, 1.2 equiv) was added and the resulting colorless solution was stirred at 23° C. for 18 h. The reaction mixture was diluted with H2O (100 mL) and extracted with CH2Cl2 (3×75 mL). The combined organic layers were dried over magnesium sulfate (MgSO4), gravity filtered, and concentrated by rotary evaporation to afford a yellow oil (1.6 g, 99%): 1H NMR (300 MHz, CDCl3) δ 5.98 (m, 1H), 5.37-5.24 (m, 2H), 4.33 (dt, J=6, 1 Hz, 2H), 3.10 (s, 3H), 1.49 (s, 9H).

Workup

  1. customThe resulting bubbling white mixture
  2. additionwas added
  3. extractionextracted with CH2Cl2 (3×75 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate (MgSO4), gravity
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-2f98fc7b7b0f4cd784c668559b1958af
Source dataset
uspto-grants-2013_09
Patent number
US08536331B2

Reaction notes

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