Isopropenyl chloroformate → HCID 90445233, compound

HRID 1049303Notes

Reaction equation

HRID 1049303 reaction equation
[CH2:1]([O:3][C:4]([CH3:9])([CH3:8])[C:5]([NH2:7])=[O:6])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:21]([O:23][C:24]([CH3:26])=[CH2:25])=[O:22]>C1COCC1>[CH2:1]([O:3][C:4]([CH3:9])([CH3:8])[C:5]([NH:7][C:21](=[O:22])[O:23][C:24]([CH3:26])=[CH2:25])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 904032482-Ethoxy-2-methylpropanamide

Product 1

HCID 90445233HCID 90445233, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −78° C. solution of 2-ethoxy-2-methylpropanamide (1.1 g, 8.39 mmol) in THF (37 mL), under Ar, was treated with LiHMDS (1 M in THF, 11 mL, 11 mmol) stirred for 0.5 h, treated with a solution of isopropenyl chloroformate (1.46 g, 12.10 mmol) in THF (2 mL), stirred for 15 minutes at −78° C. then slowly warmed to RT as the cooling bath expired. The mixture was treated with satd. NH4Cl, extracted with DCM (4×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford prop-1-en-2-yl (2-ethoxy-2-methylpropanoyl)carbamate (2.0 g, 84%) as an orange oil.

Workup

  1. stirringstirred for 15 minutes at −78° C.
  2. additionThe mixture was treated with satd
  3. extractionNH4Cl, extracted with DCM (4×)
  4. dry with materialthe combined organics were dried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6b6c73baef554542819cd28f5857e950
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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