Sulfuric Acid → 4-Trimethylsilyl-3-butyn-1-ol

HRID 2291837Notes

Reaction equation

HRID 2291837 reaction equation
C([Mg]Br)C.[CH2:5]([OH:9])[CH2:6][C:7]#[CH:8].Cl[Si:11]([CH3:14])([CH3:13])[CH3:12].S(=O)(=O)(O)O>O1CCCC1>[CH3:12][Si:11]([CH3:14])([CH3:13])[C:8]#[C:7][CH2:6][CH2:5][OH:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6397ChlorotrimethylsilaneHCID 135663-Butyn-1-OLHCID 178418443HCID 178418443, compound

Product 1

HCID 27608274-Trimethylsilyl-3-butyn-1-olYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 mol of ethyl magnesium bromide (2.0 molar solution in tetrahydrofuran) is cooled in an ice bath and a solution of 50.5 g of 3-butyn-1-ol (0.72 mol) in 50 ml of tetrahydrofuran is slowly added. After addition is complete, the mixture was allowed to warm to room temperature and was stirred overnight. The mixture was then cooled in an ice bath and 254 ml (2 mol) of chlorotrimethylsilane was slowly added. This mixture was heated under reflux for two hours and then cooled to 20° C. and 800 ml of 1.4M aqueous sulfuric acid were added. The mixture was extracted with diethyl ether and the ether solution was dried and concentrated under vacuum. The residue was distilled to yield 72.8 g of 4-trimethylsilyl-3-butyne-1-ol, bp 43°-48° C. at 1 mm Hg.

Workup

  1. additionAfter addition
  2. temperatureThe mixture was then cooled in an ice bath
  3. temperatureThis mixture was heated
  4. temperatureunder reflux for two hours
  5. temperaturecooled to 20° C.
  6. extractionThe mixture was extracted with diethyl ether
  7. dry with materialthe ether solution was dried
  8. concentrationconcentrated under vacuum
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-311a689646b5470db5a98a39ea0636f9
Source dataset
uspto-grants-1989_01
Patent number
US04798841

Reaction notes

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