Triacetoxyperiodinane → HCID 118307094, compound

HRID 921193Notes

Reaction equation

HRID 921193 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([O:10][C@H:11]([CH2:13][CH:14]=[CH2:15])[CH3:12])[CH:3]=1.[CH3:16]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[CH3:16][C:7]1[CH:2]=[CH:3][C:4]([O:10][C@H:11]([CH2:13][CH:14]=[CH2:15])[CH3:12])=[C:5]([CH:6]=1)[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118307019HCID 118307019, compound

Product 1

HCID 118307094HCID 118307094, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture (S)-(4-methyl-2-(pent-4-en-2-yloxy)phenyl)methanol (100 mg, 0.485 mmol), Dess-Martin periodinane (247 mg, 0.582 mmol) in DCM (5 mL) was stirred at rt for 1 h. It was then diluted with EtOAc and washed with sat. NaHCO3 and water. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (S)-5-methyl-2-(pent-4-en-2-yloxy)benzaldehyde (90 mg, 91%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.44 (s, 1H), 7.75 (d, J=8.1 Hz, 1H), 6.87-6.78 (m, 2H), 5.88 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.21-5.10 (m, 2H), 4.59 (sxt, J=6.1 Hz, 1H), 2.63-2.51 (m, 1H), 2.51-2.42 (m, 1H), 2.40 (s, 3H), 1.40 (d, J=6.1 Hz, 3H).

Workup

  1. washwashed with sat. NaHCO3 and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain an oil, which
  6. customwas then purified by biotage
  7. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-8620d6e201b6401db63fc067d2d33ebe
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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