20770-41-6 → HCID 85865003, compound

HRID 1796575Notes

Reaction equation

HRID 1796575 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([CH3:29])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[PH:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=1[CH3:28].[CH2:30]([O:32]C(OCC)CBr)[CH3:31].[PH2-].[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1COCC1>[C:11]1([CH3:29])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[P:19]([CH2:31][CH:30]=[O:32])[C:20]1[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26]

Participants

7

Reactant 4

HCID 6274520770-41-6HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 3251421Potassium bis(trimethylsilyl)amideHCID 4590857Dimesitylphosphine

Product 1

HCID 85865003HCID 85865003, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

KHMDS (35 mL of a 0.5 M solution in toluene, 17.5 mmol, Aldrich) 35 was added to a solution of dimesitylphosphine (4.1 g, 15.8 mmol) in THF (50 mL) at −78° C. After stirring for 20 min at −78° C. bromoacetaldehyde diethylacetal (2.85 mL, 19 mmol, Aldrich) was added dropwise to the solution of potassium phosphide. The solution was stirred for 5 min at −78° C., warmed to RT and stirred for 30 min at RT. Assay by 31P-NMR (crude reaction mixture) showed the formation of product (−29.5 ppm). The solvent was evaporated, the residue was flushed through a 6×3.3 cm plug of silica gel and toluene was removed (aspirator) to afford the product as a yellow oil. The product was dissolved in a mixture of degassed acetone (60 mL) and 5% aq. HCl (30 mL) and refluxed under Ar for 2.5 h. A saturated, degassed solution of NaHCO3 (100 mL) was added to the reaction mixture followed by extraction with degassed CH2Cl2 (3×50 mL). The solution was evaporated under Ar followed by filtration through a plug of silica gel (9×3.6 cm; Ar atmosphere), CH2Cl2 eluent, collecting 250 mL. Evaporation afforded product as a very air-sensitive white solid, 4.1 g (83.1%). 31P{1H} NMR (CD2Cl2): −35.6 ppm (s).

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for 30 min at RT
  3. customAssay by 31P-NMR (crude reaction mixture)
  4. customThe solvent was evaporated
  5. customthe residue was flushed through a 6×3.3 cm plug of silica gel and toluene
  6. customwas removed (aspirator)

Sources & evidence

ORD record
ord-06a57014a49d4ecf92b26b854081f05e
Source dataset
uspto-grants-2006_04
Patent number
US07030200B2

Reaction notes

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