4-[[(tetrahydro 2H-pyran-2-yl) oxy] methyl] 2-thiazole carboxaldehyde → alpha-ethynyl 4-[[(tetrahydro 2H-pyran-2-yl) oxy] methyl] 2-thiazole methanol

HRID 1608538Notes

Reaction equation

HRID 1608538 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[C:11]([CH:14]=[O:15])[S:12][CH:13]=1.[C:16]([Mg]Br)#[CH:17]>CCCCCC.C(OCC)(=O)C>[C:16]([CH:14]([C:11]1[S:12][CH:13]=[C:9]([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[N:10]=1)[OH:15])#[CH:17]

Participants

4

Reactant 2

HCID 542483094-[[(tetrahydro 2H-pyran-2-yl) oxy] methyl] 2-thiazole carboxaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 53736243alpha-ethynyl 4-[[(tetrahydro 2H-pyran-2-yl) oxy] methyl] 2-thiazole methanol

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The product was prepared starting with the product of Stage B and ethynyl magnesium bromide using the procedure of Example 1 to obtain the desired product with a Rf=0.11 (hexane-ethyl acetate (7-3)).

Workup

  1. customThe product was prepared

Sources & evidence

ORD record
ord-4fe8586dde454c96aa6deeca9303f204
Source dataset
uspto-grants-1995_03
Patent number
US05395845

Reaction notes

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