HCID 61101590, compound → STK163074

HRID 2378302Notes

Reaction equation

HRID 2378302 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[OH:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 61101590HCID 61101590, compound

Product 1

HCID 1519947STK163074

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(4-methoxy-phenyl)-methanol (2.03 g crude, 7.5 mmol) in CH2Cl2 (20 mL) at room temperature was added activated MnO2 powder (3.4 g, 39 mmol) and kept adding 2˜3 equivalents of MnO2 every 3˜5 h until HPLC showed disappearance of the starting material. The black suspension was filtered through a Celite pad, concentrated in vacuo to give (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(4-methoxy-phenyl)-methanone as an brown oil (2.09 g, 103% crude yield): 1H NMR (CDCl3) δ 3.88 (s, 3H, OCH3), 4.30-4.34 (m, 4H, CH2CH2), 6.91-6.97 (m, 3H, Ar), 7.26-7.36 (m, 2H, Ar), 7.78-7.81 (m, 2H, Ar). The product was used in the next step without further purification.

Workup

  1. filtrationThe black suspension was filtered through a Celite pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b99041be36346bfacb53ffeaef64ece
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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