HCID 86690128, compound → HCID 86690129, compound

HRID 520431Notes

Reaction equation

HRID 520431 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13][C:14]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1>C(Cl)Cl>[CH:13]([C:14]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)=[O:12]

Participants

4

Reactant 2

HCID 86690128HCID 86690128, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86690129HCID 86690129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat PCC was added to a stirred suspension of powdered 4 Å molecular sieve (˜0.5 g) in a solution of ethyl 2-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate (165 mg, 0.877 mmol) in DCM (6 mL) and the mixture was stirred at rt 5 h. The suspension was filtered through a plug of silica gel and eluted with (0-2% EtOAc in DCM) afford ethyl 2-formyltetrahydro-2H-pyran-2-carboxylate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.53 (s, 1H), 4.35-4.20 (m, 2H), 3.97-3.77 (m, 2H), 2.23-2.12 (m, 1H), 1.90-1.77 (m, 1H), 1.77-1.69 (m, 1H), 1.64-1.56 (m, 3H), 1.32 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe suspension was filtered through a plug of silica gel
  2. washeluted with (0-2% EtOAc in DCM)

Sources & evidence

ORD record
ord-df4e113675a24271b576a0a374a7bfb7
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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