Ammonium Chloride → 1-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol

HRID 1029660Notes

Reaction equation

HRID 1029660 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH2:12]([O:15][C:16]([N:18]([CH2:26][CH:27]=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH:13]=[CH2:14].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:12]([O:15][C:16]([N:18]([CH2:26][CH:27]([OH:28])[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH:13]=[CH2:14]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 151172972-(N-allyloxycarbonyl-N-benzylamino)acetaldehydeHCID 178418339Butyllithium

Product 1

HCID 151172981-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (trimethylsilyl)acetylene (23.75 ml) in tetrahydrofuran (250 ml) was added a 1.6M solution of butyllithium in hexane (105 ml) below -60° C. After stirring for one hour, a solution of 2-(N-allyloxycarbonyl-N-benzylamino)acetaldehyde (32.86 g) in tetrahydrofuran (30 ml) was added to the mixture below -60° C. The solution was stirred at the same condition for one hour and an aqueous saturated ammonium chloride (100 ml) was added to the reaction mixture below -60° C. After stirring at the ambient temperature for one hour, ethyl acetate (300 ml) was poured into the mixture. The solution was washed with brine (150 ml×2), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (300 g) and eluted with a mixture of hexane and ethyl acetate (9:1, V/V) to give 1-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol (19.77 g) as a syrup.

Workup

  1. stirringThe solution was stirred at the same condition for one hour
  2. stirringAfter stirring at the ambient temperature for one hour
  3. washThe solution was washed with brine (150 ml×2)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of hexane and ethyl acetate (9:1, V/V)

Sources & evidence

ORD record
ord-f9d8bc74754e416397c8ddde83ac970a
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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