Hydrochloric Acid → HCID 21527997, compound

HRID 1658566Notes

Reaction equation

HRID 1658566 reaction equation
[CH3:1][CH:2]([CH3:5])[C:3]#[CH:4].C([Li])CCC.[CH3:11][Si:12](Cl)([CH3:14])[CH3:13].[CH:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].Cl>CCCCCC.CCOCC>[OH:21][CH:16]([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]([CH3:5])([CH3:1])[C:3]#[C:4][Si:12]([CH3:14])([CH3:13])[CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8063PentanalHCID 690193-Methylbut-1-yneHCID 178418339Butyllithium2×

Product 1

HCID 21527997HCID 21527997, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent2×

Procedure

To a solution of 6.8 parts of 3-methyl-1-butyne in 50 parts by volume of ether, cooled to -40°, is added dropwise 46.7 parts by volume of 2.14 M n-butyl lithium in hexane. The resulting solution is allowed to warm to room temperature and is stored at that temperature for about 15-30 minutes, then cooled again to -40° and 10.8 parts of trimethylsilyl chloride is added. The temperature is allowed to rise to room temperature and the mixture is stirred for about 1 hour, at the end of which time 46.7 parts by volume of 2.14 M n-butyl lithium in hexane is added dropwise. The resulting reaction mixture is heated at the reflux temperature for about 18 hours, then is cooled to about -10° and 8.6 parts of valeraldehyde is added. The mixture is allowed to warm to room temperature, then is stirred for about 2 hours and poured into a mixture of ether and dilute hydrochloric acid. The ether layer is washed with water, dried over anhydrous sodium sulfate, stripped of solvent under reduced pressure and distilled under vacuum to afford (4(RS)-hydroxy-3,3-dimethyl-1-octynyl)trimethylsilane, characterized by an infrared absorption maximum of about 2160 reciprocal centimeters.

Workup

  1. temperaturecooled again to -40°
  2. customto rise to room temperature
  3. additionis added dropwise
  4. customThe resulting reaction mixture
  5. temperatureis heated at the reflux temperature for about 18 hours
  6. temperatureis cooled to about -10°
  7. temperatureto warm to room temperature
  8. washThe ether layer is washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-f5a8acd3e7f04febb88b7a9ab610dbe0
Source dataset
uspto-grants-1976_06
Patent number
US03965143

Reaction notes

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