Ethyl allyl(2,2-dimethoxyethyl)carbamate → Ethyl allyl(2-oxoethyl)carbamate

HRID 1842703Notes

Reaction equation

HRID 1842703 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]([CH2:11][CH:12]=[CH2:13])[C:6](=[O:10])[O:7][CH2:8][CH3:9]>C(O)=O>[O:2]=[CH:3][CH2:4][N:5]([CH2:11][CH:12]=[CH2:13])[C:6](=[O:10])[O:7][CH2:8][CH3:9]

Participants

3

Reactant 1

HCID 10943907Ethyl allyl(2,2-dimethoxyethyl)carbamate2×

Product 1

HCID 11084330Ethyl allyl(2-oxoethyl)carbamateYield 100.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of ethyl N-(2,2-dimethoxyethyl)-N-prop-2-enylcarbamate (Intermediate 42, 1218 g, 2.79 mol) in HCOOH (4.2 L) was refluxed for 0.5 h. Then crushed ice was added to quench the reaction, the mixture was extracted with CH2Cl2 (2 L×3). The combined organic solutions were washed with sat. NaHCO3 (3 L), dried (Na2SO4) and concentrated in vacuo to give the title compound (480 g, 50%) as yellow oil; 1H NMR: (CDCl3) 1.15-1.32 (3H, m), 3.89-4.00 (4H, m), 4.07-4.16 (2H, m), 5.10 (2H, m), 5.73 (1H, m), 9.53 (1H, s).

Workup

  1. additionThen crushed ice was added
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with CH2Cl2 (2 L×3)
  5. washThe combined organic solutions were washed with sat. NaHCO3 (3 L)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e1e22d0f5b449b5b0fdb8df899e96af
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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