Chlorotrimethylsilane → HCID 10923628, compound

HRID 1647772Notes

Reaction equation

HRID 1647772 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>C1COCC1.CCCCCC>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][Si:20]([CH3:22])([CH3:21])[CH3:19])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 108673065-(t-Butyldimethylsilyloxy)pent-1-yneHCID 178418339Butyllithium

Product 1

HCID 10923628HCID 10923628, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 135 g (682 mmol, 1.0 equiv.) of 1-t-butyldimethylsilyloxy-4-pentyne in 700 mL of THF at -780° C. was added 311 mL (716 mmol, 1.05 equiv.) of a 2.3M solution of n-butyllithium in hexane. The -78° C. bath was removed and the reaction temperature was monitored as it rose to 0° C. The reaction was recooled to -78° C. and 90.8 mL (716 mmol, 1.05 equiv.) of trimethylsilyl chloride was added dropwise. The reaction was then allowed to warm slowly in the cold bath for 16 hours. The reaction was diluted with 2000 mL of hexane, washed with 500 mL of saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting liquid was distilled at 71°-74° C. at 0.05 mm Hg to yield 168 g (91%) of 1-t-butyldimethylsilyloxy-5-trimethylsilyl-4-pentyne.

Workup

  1. customThe -78° C. bath was removed
  2. customrose to 0° C
  3. customwas recooled to -78° C.
  4. temperatureto warm slowly in the cold bath for 16 hours
  5. washwashed with 500 mL of saturated aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationThe resulting liquid was distilled at 71°-74° C. at 0.05 mm Hg

Sources & evidence

ORD record
ord-e74c5b38d1da43578869a387dee8d657
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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