Trimethylsilylacetylene → HCID 18616579, compound

HRID 1264037Notes

Reaction equation

HRID 1264037 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[Li]CCCC.C([O:16][C:17]([NH:19][C:20]([CH3:24])([CH3:23])[CH:21]=[O:22])=O)(C)(C)C>C1COCC1>[CH3:23][C:20]1([CH3:24])[CH:21]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[O:22][C:17](=[O:16])[NH:19]1

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 18616579HCID 18616579, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cold (−78° C.), stirred solution of (trimethylsilyl)acetylene (4.42 g, 45.0 mmol) in anhydrous THF (20 mL) was treated with nBuLi (18 mL, 45.0 mmol) under nitrogen. The colorless solution was stirred for 30 minutes and followed by the addition of 2-(tert-butoxycarbonylamino)-2-methyl propionaldehyde (2.80 g, 15 mmol) in anhydrous THF (20 mL). The reaction was warmed up to room temperature, stirred for 2 hours, and quenched with water. After removal of THF, the residue was partitioned between ether (150 mL) and water (100 mL). The separated organic layer was washed with brine (100 mL), dried over sodium sulfate, and concentrated to give the crude 4,4-Dimethyl-5-trimethylsilylethynyl-2-oxazolidinone (100%) as yellow oil which was carried to the next step.

Workup

  1. stirringstirred for 2 hours
  2. customquenched with water
  3. customAfter removal of THF
  4. customthe residue was partitioned between ether (150 mL) and water (100 mL)
  5. washThe separated organic layer was washed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-57549f7b4fde4d088f578c7806c65d79
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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