Acetyl chloride → 4-(Tetrahydro-pyran-2-yloxy)-but-3-yn-2-one
Reaction equation
C(O[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)C#C.C([Li])CCC.C(Cl)(=[O:18])C.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>[Cl-].[Zn+2].[Cl-]>[O:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[O:20][C:24]#[C:23][C:22](=[O:18])[CH3:21]Participants
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere tetrahydro-2-(2-propynyloxy)-2H-pyran (636 mL, 4.52 mmol) was dissolved in dry tetrahydrofuran (20 mL) and cooled to −78° C. n-Butyllithium (2.5 M in hexanes, 2.03 mL, 5.06 mmol) was added drop-wise. Zinc chloride (629 mg, 4.51 mmol) dissolved in tetrahydrofuran (5 mL) was added drop-wise and the reaction mixture was allowed to warm to 0° C. Acetyl chloride (0.35 mL, 4.93 mmol) was added followed by heating to 40° C. for 45 min. The reaction was quenched with saturated aqueous ammonium chloride. Ethyl acetate was added and the phases were separated. The organic phase was washed with saturated aqueous ammonium chloride (2×) and brine, dried over magnesium sulphate, filtered and concentrated in vacuo to give 4-(tetrahydro-pyran-2-yloxy)-but-3-yn-2-on as the crude product.
Workup
- additionwas added drop-wise
- additionwas added drop-wise
- temperatureby heating to 40° C. for 45 min
- customThe reaction was quenched with saturated aqueous ammonium chloride
- additionEthyl acetate was added
- customthe phases were separated
- washThe organic phase was washed with saturated aqueous ammonium chloride (2×) and brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-982c22904c9b480ab6f802f48b385592
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362024B2
Reaction notes
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