HCID 69203973, compound → HCID 69205734, compound

HRID 2378281Notes

Reaction equation

HRID 2378281 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([CH:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=3)[OH:13])[CH:10]=[CH:11][C:2]1=2>C(Cl)Cl.O=[Mn]=O>[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([C:12]([C:14]3[CH:15]=[C:16]([O:22][CH3:23])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=3)=[O:13])[CH:10]=[CH:11][C:2]1=2

Participants

4

Reactant 1

HCID 69203973HCID 69203973, compound

Product 1

HCID 69205734HCID 69205734, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of (3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-(3,5-dimethoxy-phenyl)-methanol (1.8 g, 5.7 mmol) and MnO2 (2.6 g, 30 mmol) in methylene chloride (40 mL) was stirred at room temperature for 4 h. More MnO2 (1.3 g) was added and kept for overnight. The suspension was filtered thru a pad of Celite. Removal of solvent gave (3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-(3,5-dimethoxy-phenyl) -methanone as an oil (1.3 g, 72% yield): 1H NMR (CDCl3) δ 2.22-2.28 (m, 2H, CH2), 3.82 (s, 6H, 2CH3), 4.28-4.31 (m, 4H, 2CH2), 6.64 (t, J=2 Hz, 1H, Ar), 6.88 (d, J=2 Hz, 2H, Ar), 6.99 (d, J=8 Hz, 1H, Ar), 7.42 (dd, J=1, 9 Hz, 1H, Ar), 7.48 (d, J=2 Hz, 1H, Ar).

Workup

  1. waitkept for overnight
  2. filtrationThe suspension was filtered
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-335e8704cdfe42a7b86f22999bb8edbc
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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