Triacetoxyperiodinane → (4-Chloro-phenyl)-(tetrahydro-pyran-2-yl)-methanone

HRID 449120Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[OH:9])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (4-chloro-phenyl)-(tetrahydro-pyran-2-yl)-methanol (70.00 mg, 0.30 mmol) in DCM (10 mL) was added NaHCO3 (259.4 mg, 3.08 mmol) and Dess-Martin periodinane (196.4 mg, 0.46 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hrs. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (eluting with 5% AcOEt in Hexane). 1H NMR (400 MHz, MeOD) δ 1.52-2.02 (m, 6H), 3.65-3.77 (m, 1H), 4.04-4.17 (m, 1H), 4.82-4.88 (m, 1H), 7.54 (d, J=8.50 Hz, 2H), 8.02 (d, J=8.50 Hz, 2H).

Workup

customThe solvent was then removed under reduced pressure
customthe resulting residue was purified by a flash chromatography (eluting with 5% AcOEt in Hexane)

Sources & evidence

ORD record: ord-11051b45816145c1974c32c23a097838
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

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