Hydrochloric Acid → Methyl [(1-methyl-2-propynyl)oxy]acetate

HRID 478302Notes

Reaction equation

HRID 478302 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:7])[C:5]#[CH:6].Br[CH2:9][C:10]([O:12][CH3:13])=[O:11].Cl>O1CCCC1>[CH3:3][CH:4]([O:7][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]#[CH:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 162393-Butyn-2-olHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 18619750Methyl [(1-methyl-2-propynyl)oxy]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mechanically stirred suspension of sodium hydride (60% dispersion in mineral oil, 10 g, 0.25 mol) in tetrahydrofuran (160 mL) at 0° C. under nitrogen was treated with a solution of (±)-3-butyn-2-ol (21 g, 0.30 mol) in tetrahydrofuran (35 mL) over 30 minutes, stirred for 35 minutes, treated with a solution of methyl bromoacetate in tetrahydrofuran (50 mL) over 10 minutes, stirred for 30 minutes at 0° C., stirred at ambient temperature for 16 hours and treated with 2M HCl (150 mL). The organic layer was isolated and the aqueous layer was extracted with ethyl acetate (2×, 100 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered, concentrated and distilled under vacuum to provide the title compound (20 g).

Workup

  1. stirringstirred for 30 minutes at 0° C.
  2. stirringstirred at ambient temperature for 16 hours
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×, 100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-5f438e9a9570423aaa4ccf0aff183201
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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