Diethyl Ether → HCID 12786232, compound

HRID 126722Notes

Reaction equation

HRID 126722 reaction equation
[Mg].[CH2:2](Br)[C:3]#C.[CH3:6][S:7][CH2:8][CH2:9][C:10](=[O:12])[CH3:11].[CH3:13]COCC>>[OH:12][C:10]([CH3:13])([CH2:9][CH2:8][S:7][CH3:6])[CH2:11][C:2]#[CH:3]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 7842Propargyl bromideHCID 619224-(Methylthio)-2-butanoneHCID 5462224Magnesium

Product 1

HCID 12786232HCID 12786232, compound

Procedure

To a stirred mixture of 6.6 g. (0.275 moles) of magnesium and 116 mg. of mercuric chloride in 35 ml. of ether is added, dropwise under argon atmosphere, 35.2 g. of propargyl bromide (80% solution in toluene) and 25 g. (0.21 moles) of methylmercaptobutane-3-one [D. B. Reisner, J. Am. Chem. Soc., 78, 2132 (1956)] in 100 ml. of ether at a rate to maintain gentle refluxing. After stirring at the reflux temperature for 35 minutes, the cooled mixture is quenched by dropwise addition of 140 ml. of saturated ammonium chloride solution. The ether phase is separated, washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation of the residual oil provides 27.4 g. (82%) of product as a colorless oil; b.p. 114°-115° C. (7-8 mm.).

Workup

  1. additionTo a stirred mixture of 6.6 g
  2. customthe cooled mixture is quenched by dropwise addition of 140 ml
  3. customThe ether phase is separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationDistillation of the residual oil
  7. customprovides 27.4 g

Sources & evidence

ORD record
ord-503ffd60b4c04ddb8b1ce060ccb8fec5
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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