Triacetoxyperiodinane → methyl 4-(tetrahydro-2H-pyran-4-carbonyl)benzoate

HRID 1892707Notes

Reaction equation

HRID 1892707 reaction equation
[OH:1][CH:2]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10]C)=[O:8])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:17]1[CH2:18][CH2:19][CH:14]([C:2]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:12][CH:13]=2)=[O:1])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68156522ethyl 4-(hydroxy(tetrahydro-2H-pyran-4-yl)methyl)benzoate

Product 1

HCID 68156933methyl 4-(tetrahydro-2H-pyran-4-carbonyl)benzoateYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A round bottom flask was charged with ethyl 4-(hydroxy(tetrahydro-2H-pyran-4-yl)methyl)benzoate (1.9 g, 7.2 mmol), the Dess-Martin reagent (3.66 g, 8.63 mmol) and DCM (15 mL). The reaction was stirred at room temperature overnight. Reaction diluted with DCM and solid filtered off. The mother liquor concentrated and loaded onto a silica gel column. Purification by silica gel flash chromatography (ethyl acetate/DCM) provide methyl 4-(tetrahydro-2H-pyran-4-carbonyl)benzoate (290 mg, mmol) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.75-1.96 (m, 4H) 3.45-3.62 (m, 3H) 3.97 (s, 3H) 4.07 (dt, J=11.88, 3.25 Hz, 2H) 7.98-8.02 (m, 2H) 8.12-8.17 (m, 2H); MS (M−1): 246.8.

Workup

  1. customReaction
  2. filtrationfiltered off
  3. concentrationThe mother liquor concentrated
  4. customPurification by silica gel flash chromatography (ethyl acetate/DCM)

Sources & evidence

ORD record
ord-8ab84c0a04544411aa39520acb9fd07f
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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