Isopropenyl chloroformate → HCID 131736004, compound

HRID 1049337Notes

Reaction equation

HRID 1049337 reaction equation
[F:1][C:2]([F:11])([F:10])[O:3][CH2:4][CH2:5][CH2:6][C:7]([NH2:9])=[O:8].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:23]([O:25][C:26]([CH3:28])=[CH2:27])=[O:24]>C1COCC1>[F:1][C:2]([F:10])([F:11])[O:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:23](=[O:24])[O:25][C:26]([CH3:28])=[CH2:27])=[O:8]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 88929351HCID 88929351, compound

Product 1

HCID 131736004HCID 131736004, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −78° C. mixture of 4-(trifluoromethoxy)butanamide (175 mg, 1.023 mmol) in THF (5 mL) was treated drop wise with LiHMDS (1.0M in THF, 1.33 mL, 1.33 mmol), stirred for 0.5 h, then treated drop wise with a solution of isopropenyl chloroformate (0.129 mL, 1.176 mmol) in THF (1 mL). The mixture was allowed to warm to RT, treated with satd. NaHCO3 and extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and concentrated to afford prop-1-en-2-yl (4-(trifluoromethoxy)butanoyl)carbamate (100% yield assumed).

Workup

  1. additiontreated with satd
  2. extractionNaHCO3 and extracted with EtOAc (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-904bbdd7721347c1a8e9ffcc0d85765b
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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