HCID 86690108, compound → HCID 86690109, compound

HRID 520400Notes

Reaction equation

HRID 520400 reaction equation
[OH:1][CH:2]1[CH2:7][O:6][CH:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:14][C:8]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][O:6]1)([CH3:13])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 86690108HCID 86690108, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86690109HCID 86690109, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 2-(5-hydroxytetrahydro-2H-pyran-2-yl)-2-methylpropanoate (187 mg, 0.925 mmol) in DCM (5 mL) containing 4 Å molecular seives (˜250 mg) was added PCC (259 mg, 1.202 mmol). The reaction mixture was stirred at rt for 3 h, then loaded onto a silica gel column and eluted with 10-20% EtOAc in DCM to afford methyl 2-methyl-2-(5-oxotetrahydro-2H-pyran-2-yl)propanoate as a clear oil (105 mg). 1H NMR (400 MHz, CDCl3) δ ppm 4.18 (1H, dd, J=16.56, 1.76 Hz), 3.87-4.01 (2H, m), 3.73 (3H, s), 2.59-2.69 (1H, m), 2.48 (1H, dt, J=17.13, 8.63 Hz), 1.93-2.04 (2H, m), 1.27 (3H, s), 1.15-1.24 (3H, m).

Workup

  1. washeluted with 10-20% EtOAc in DCM

Sources & evidence

ORD record
ord-eb85964ffbdd4abd97d60489597dc7ac
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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