3,4-dihydro-2H-pyran → HCID 54519216, compound

HRID 345191Notes

Reaction equation

HRID 345191 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][C@@H:8]([C@H:11]([OH:13])[CH3:12])[C:9]#[CH:10].C(=O)([O-])[O-].[K+].[K+]>Cl.C(OCC)C>[CH3:7][C@@H:8]([C@H:11]([O:13][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH3:12])[C:9]#[CH:10]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 13856127HCID 13856127, compound

Product 1

HCID 54519216HCID 54519216, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

To dihydropyran (1.3 g) cooled in an ice bath was added (3R*,4R*)-3-methyl-1-pentyn-4-ol (1.3 g) followed by concentrated hydrochloric acid (1 drop) and the mixture was stirred for 16 h at room temperature. Potassium carbonate (100 mg) was added and the mixture stirred for 15 minutes. Diethyl ether (10 ml) was added and the mixture was filtered before evaporation to an oil. The residue was distilled to give the title compound (1.2 g) (b.p. 130°-5° C. at 10 mm Hg).

Workup

  1. stirringthe mixture stirred for 15 minutes
  2. filtrationthe mixture was filtered before evaporation to an oil
  3. distillationThe residue was distilled

Sources & evidence

ORD record
ord-18584f81b66a4ebbb0c6eab27a90a3fd
Source dataset
uspto-grants-1991_10
Patent number
US05055596

Reaction notes

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