Hydrochloric Acid → HCID 13005739, compound

HRID 2042763Notes

Reaction equation

HRID 2042763 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].CC(C)([O-])C.[K+].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>C1COCC1.CCOCC>[CH3:1][C:2]([O:6][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])([CH3:3])[C:4]#[CH:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 82582-Methyl-3-butyn-2-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 13005739HCID 13005739, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.87 g (10.32 mmol) of 2-methylbut-3-yn-2-ol in 20 ml of anhydrous THF is cooled to 0-5° C. with an ice bath and then 10.32 ml (10.32 mmol) of 1.0M potassium t-butoxide in THF (Aldrich) are added. Stirring is carried out under cold conditions for 10 minutes and then 1.89 g (11.35 mmol) of ethyl bromoacetate are added. The reaction mixture is stirred at ambient temperature for 45 minutes and then 0.1 N aqueous HCl and ether are added. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. 1.45 g of the expected product are obtained in the form of a yellow oil which is used without subsequent purification. Yield=83%.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 45 minutes
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3f4e5f358e174ea9a7667617a322ce93
Source dataset
uspto-grants-2013_11
Patent number
US08586602B2

Reaction notes

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