Triacetoxyperiodinane → 2H-1,5-Benzodioxepin-3(4H)-one

HRID 2090110Notes

Reaction equation

HRID 2090110 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]([OH:12])[CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][C:3](=[O:12])[CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 139029903,4-dihydro-2H-benzo[b][1,4]dioxepin-3-ol

Product 1

HCID 113097002H-1,5-Benzodioxepin-3(4H)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3,4-dihydro-2H-1,5-benzodioxepin-3-ol (1 g, 6.02 mmol) in dichloromethane (20 ml) was added Dess-Martin periodinane (2.8 g, 6.60 mmol). The mixture was stirred overnight at 25° C., and then purified by flash chromatography on a Biotage Horizon, 40M column, eluting with 1 column volume of 100% dichloromethane, followed by a gradient of 0 to 100% ethyl acetate in dichloromethane over 10 column volumes, to provide the title compound (964 mg, 5.87 mmol, 98% yield). 1H NMR (500 MHz, CDCl3): δ 6.99 (m, 4H), 4.72 (s, 4H).

Workup

  1. custompurified by flash chromatography on a Biotage Horizon, 40M column
  2. washeluting with 1 column volume of 100% dichloromethane

Sources & evidence

ORD record
ord-619e8e0a15e340fdac7262e141c4523b
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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