HCID 69205118, compound → HCID 69205163, compound

HRID 2378254Notes

Reaction equation

HRID 2378254 reaction equation
[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[CH:8]=[C:9]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=2)[OH:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[CH:8]=[C:9]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=2)=[O:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69205118HCID 69205118, compound

Product 1

HCID 69205163HCID 69205163, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3-ethoxy-4-methoxy-phenyl)-methanol (6.5 g, 15.6 mmol) in CH2Cl2 (200 mL) was added manganese dioxide (2.65 g, 26.1 mmol), and the mixture was stirred at ambient temperature for 16 h. Manganese dioxide (2.65 g, 26.1 mmol) was again added, and stirring proceeded for an additional 7 h. The mixture was filtered through Celite, and the sicciate was washed with CH2Cl2 (50 mL). The filtrate was evaporated, providing [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3-ethoxy-4-methoxy-phenyl)-methanone as an oil (6.2 g, 96% yield): 1H NMR (CDCl3) δ 0.17 (s, 6H, 2SiCH3), 1.00 (s, 9H, SiC(CH3)3), 1.49 (t, J=7.0 Hz, 3H, OCH2CH3), 3.89 (s, 3H, OCH3), 3.95 (s, 3H, OCH3), 4.16 (q, J=7.0 Hz, 2H, OCH2CH3), 6.87-6.92 (m, 2H, Ar), 7.33-7.43 (m, 4H, Ar).

Workup

  1. stirringstirring
  2. waitproceeded for an additional 7 h
  3. filtrationThe mixture was filtered through Celite
  4. washthe sicciate was washed with CH2Cl2 (50 mL)
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a470a470903a481bac4832105bcb6f19
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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