Tetrahydro-2H-pyran-2-carbaldehyde → (4-Chloro-phenyl)-(tetrahydro-pyran-2-yl)-methanol

HRID 449121Notes

Reaction equation

HRID 449121 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH:7]=[O:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1>C1COCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:7]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[OH:8])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 11040661Tetrahydro-2H-pyran-2-carbaldehydeHCID 178478191HCID 178478191, compound

Product 1

HCID 62212660(4-Chloro-phenyl)-(tetrahydro-pyran-2-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of tetrahydro-pyran-2-carbaldehyde (114.00 mg, 1.00 mmol) in THF (10 mL) was added 4-chlorophenylmagnesium bromide (1.0 M in diethyl ether, 1.5 mL, 1.50 mmol) at −78° C. The mixture was stirred at −78° C. for 2 hrs. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (eluting with 20% AcOEt in Hexane).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe resulting residue was purified by a flash chromatography (eluting with 20% AcOEt in Hexane)

Sources & evidence

ORD record
ord-3f879e724af44ade9ea779b5cbf0ce96
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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