Chloroform → HCID 20337222, compound

HRID 1706181Notes

Reaction equation

HRID 1706181 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[P:5](=[O:16])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[K].[CH2:18]([O:20][C:21]([O:23][NH:24][C:25](=[O:29])[O:26][CH2:27][CH3:28])=[O:22])[CH3:19].C(Cl)(Cl)Cl>CN(C)C=O.C(OCC)(=O)C>[CH2:27]([O:26][C:25]([N:24]([CH2:2]/[CH:3]=[CH:4]/[P:5](=[O:16])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[O:23][C:21]([O:20][CH2:18][CH3:19])=[O:22])=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 5462222PotassiumHCID 9995699HCID 9995699, compoundHCID 11446651Ethyl Ethoxycarbonyloxycarbamate

Product 1

HCID 20337222HCID 20337222, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of di-tert-butyl 3-bromo-trans- 1-propenylphosphonate (17.1 g.) in dry N,N-dimethylformamide (55 ml.) was added potassium salt of ethyl N-ethoxycarbonyloxycarbamate (11.03 g.). The reaction mixture was stirred for 10 minutes under ice-cooling and for 1.5 hours at ambient temperature. The reaction mixture was poured into ice water (400 ml.) and then the resultant mixture was extracted three times with ethyl acetate (300 ml., 200 ml. and 100 ml.). The combined ethyl acetate layer was washed three times with water (100 ml.), dried over magnesium sulfate and then concentrated under reduced pressure to give an oily residue (20.23 g.). The residue was subjected to column chromatography on silica gel (200 g.) [developing solvent: a mixture of chloroform and ethyl acetate (4:1)]. The fractions containing the object compound were collected and concentrated under reduced pressure to give an oily di-tert-butyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-trans-1-propenylphosphonate (8.84 g.).

Workup

  1. extractionthe resultant mixture was extracted three times with ethyl acetate (300 ml., 200 ml. and 100 ml.)
  2. washThe combined ethyl acetate layer was washed three times with water (100 ml.)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give an oily residue (20.23 g.)
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb60c32b90894d5ba1ae1d5867bb8156
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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