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

HRID 1460960Notes

Reaction equation

HRID 1460960 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-b9db964b80404f89b080e5da4b9b2e2f
Source dataset
uspto-grants-1991_12
Patent number
US05073561

Reaction notes

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