Trimethylsilylacetylene → HCID 18616579, compound

HRID 1594818Notes

Reaction equation

HRID 1594818 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, tne 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, tne residue
  4. customwas 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-7787048b199f4821bbe3ee705bc1816f
Source dataset
uspto-grants-2001_09
Patent number
US06284764B1

Reaction notes

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