HCID 69202506, compound → HCID 69202602, compound

HRID 2378322Notes

Reaction equation

HRID 2378322 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH3:21])[CH:12]=2)[OH:10])=[CH:5][CH:4]=1>C(Cl)Cl.O=[Mn]=O>[CH3:22][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH3:21])[CH:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 69202506HCID 69202506, compound

Product 1

HCID 69202602HCID 69202602, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-dimethylamino-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol (1.29 g, 4.3 mmol) in CH2Cl2 (30 mL) at room temperature was added activated MnO2 powder (2.1 g, 24 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 (4-dimethylamino-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanone as an brown oil (0.22 g, 17% yield): 1H NMR (CDCl3) δ 1.48 (t, J=7 Hz, 3H, CH2CH3), 3.08 (s, 6H, N(CH3)2), 3.95 (s, 3H, OCH3), 4.16 (q, J=7 Hz, 2H, CH2CH3), 6.67-6.71 (m, 2H, Ar), 6.88-6.92 (m, 1H, Ar), 7.34-7.39 (m, 2H, Ar), 7.77-7.80 (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-6d246a2b84334cc89cf4378b7e05fe7b
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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