HCID 86690110, compound → HCID 86690112, compound

HRID 520402Notes

Reaction equation

HRID 520402 reaction equation
[OH:1][CH:2]1[CH2:7][O:6][C:5]([CH3:18])([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:18][C:5]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][O:6]1

Participants

4

Reactant 2

HCID 86690110HCID 86690110, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86690112HCID 86690112, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl 5-hydroxy-2-methyltetrahydro-2H-pyran-2-carboxylate (1.1 g, 3.52 mmol) and molecular sieves (4 Å, 2 g, powdered) in DCM (20 mL) was added PCC (1.137 g, 5.27 mmol) in two portions at 0° C. The reaction mixture was stirred at rt for 17 h. The reaction mixture was directly loaded and purified on a 40 g silica gel cartridge (EtOAc/Hexane: 0 to 40%) to yield benzyl 2-methyl-5-oxotetrahydro-2H-pyran-2-carboxylate (0.47 g). 1H NMR (400 MHz, CDCl3) ppm 7.45-7.31 (m, 5H), 5.25 (s, 2H), 4.27 (d, J=17.6 Hz, 1H), 4.07 (d, J=17.3 Hz, 1H), 2.59-2.34 (m, 3H), 2.14-2.04 (m, 1H), 1.56 (s, 3H).

Workup

  1. custompurified on a 40 g silica gel cartridge (EtOAc/Hexane: 0 to 40%)

Sources & evidence

ORD record
ord-7668ec0727574db2a4c247cec6dfff15
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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