3-Bromo-1-(trimethylsilyl)-1-propyne → Diethyl (3-trimethylsilylprop-2-ynyl)phosphonate

HRID 1895949Notes

Reaction equation

HRID 1895949 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[P:11]([O-:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].Br[CH2:20][C:21]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[CH3:24][Si:23]([CH3:26])([CH3:25])[C:22]#[C:21][CH2:20][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 2733832Lithium HexamethyldisilazideHCID 3780918Diethylphosphite

Product 1

HCID 10933869Diethyl (3-trimethylsilylprop-2-ynyl)phosphonateYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of LiHMDS (1M in THF, 63.8 mL, 63.8 mmol) in anhydrous THF (162 mL) was added dropwise under stirring at −10° C. in nitrogen atmosphere diethyl phosphite (7.4 mL, 63.8 mmol). The obtained solution was stirred at the same temperature for 20 min. Afterwards, 3-bromo-1-trimethylsilyl-1-propyne (10 mL, 63.8 mmol) was dropped into and the reaction mixture was stirred at −10° C. for 2 h., then quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford 14.86 g of the title product.

Workup

  1. stirringwas stirred at −10° C. for 2 h.
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried on Na2SO4
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-0478276ce0694e7caf465e9c8e81663f
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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