Diethyl Ether → Tetrahydro-2H-pyran-3-propanal

HRID 452007Notes

Reaction equation

HRID 452007 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][CH:9]=[O:10])[CH2:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 576997533-(Oxan-3-yl)propan-1-ol

Product 1

HCID 15676001Tetrahydro-2H-pyran-3-propanalYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-(tetrahydro-2H-pyran-3-yl)propan-1-ol (10.35 g, 0.0719 mol) in CH2Cl2 (200 mL) was added Dess-Martin periodinane (61.24 g, 0.1438 mol). The mixture was stirred at rt. When the reaction was over, the solution was poured into Et2O (300 mL) and anhydrous K2CO3 (19.84 g, 0.1438 mol) was added. The mixture was filtered. The filtrate was dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified through column chromatography to give 3-(tetrahydro-2H-pyran-3-yl)propanal (8.25 g, 80%).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. dry with materialThe filtrate was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product, which
  6. customwas purified through column chromatography

Sources & evidence

ORD record
ord-3e218f9116c1411d8c5683b0ad5ce9f1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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