Diethyl Ether → HCID 53979940, compound

HRID 1651074Notes

Reaction equation

HRID 1651074 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH:7]=[C:8]([OH:17])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:11]=[CH:12][C:5]=2[CH:4]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH2:7][C:8](=[O:17])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:11]=[CH:12][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 67794182HCID 67794182, compound

Product 1

HCID 53979940HCID 53979940, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-6-hydroxy-dibenzo[a,e]cyclooctene (1.5 g) in dry dichloromethane (100 ml) was added pyridinium dichromate (4.5 g) and crushed 4A molecular sieves (2.3 g). After stirring at room temperature for 2h, diethyl ether (200 ml) was added and the reaction mixture was filtered through a plug of celite. The solvent was removed in vacuo and the residue purified by chromatography on flash silica with 5% ethyl acetate in hexane as eluent to give, as a colourless solid, the title compound (1.4 g), m.p. 104°-106° C. δ(360 MHz, CDCl3), 3.75 (3H, s, CH3O), 3.99 (2H, s, CH2 --CO), 6.73 (1H, d, J=2.7 Hz, CH=(OCH3)--CH), 6.86 (1H, dd, J=8.5 and 2.7 Hz, CH=C(OCH3)--CH), 7.01 (2H, s, Ar--CH=CH--Ar), 7.29-7.51 (4H, m, aromatics) and 8.24 (1H, dd, J=8.0 and 1.4 Hz, CH=C--CO). m/e 250 (M+). i.r. (νmax, nujol) 1665 cm-1 (CO). Found: C,81.5; H, 5.6. C17H14O2 requires: C, 81.0; H, 5.8%

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a plug of celite
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by chromatography on flash silica with 5% ethyl acetate in hexane as eluent
  5. customto give, as a colourless solid

Sources & evidence

ORD record
ord-dbe67c11155543eb92c61a350d774b29
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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