Triacetoxyperiodinane → 5-(3-((tert-butyldimethylsilyl)oxy)-2-oxopropyl)-4-methylisobenzofuran-1(3H)-one

HRID 1848549Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH:10]([OH:23])[CH2:11][C:12]1[C:13]([CH3:22])=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[O:16][CH2:15]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Si:1]([O:8][CH2:9][C:10](=[O:23])[CH2:11][C:12]1[C:13]([CH3:22])=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[O:16][CH2:15]2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-(3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl)-4-methylisobenzofuran-1(3H)-one (1.00 g, 3.0 mmol) in CH2Cl2 (30 mL) was added Dess-Martin periodinane (6.30 g, 15.0 mmol). After stirring at 25° C. for 12 h, the reaction mixture was filtered through a short pad of SiO2 with CH2Cl2 (100 mL) as the eluting solvent. After concentrating, the residue was purified by flash column chromatography (0-60% ethyl acetate in petroleum ether) to give the title compound.

Workup

filtrationthe reaction mixture was filtered through a short pad of SiO2 with CH2Cl2 (100 mL) as the eluting solvent
concentrationAfter concentrating
customthe residue was purified by flash column chromatography (0-60% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-f0ae7c7b03184ce492bcf966c1396a13
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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