Diethyl Ether → HCID 54476367, compound

HRID 1651070Notes

Reaction equation

HRID 1651070 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[CH:12]=[C:13]([OH:14])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[CH2:12][C:13](=[O:14])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 67794269HCID 67794269, compound

Product 1

HCID 54476367HCID 54476367, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-chloro-5-hydroxy-dibenzo[a,e]cyclooctene (1.5 g) in dry dichloromethane (60 ml) was added pyridinium dichromate (5.0 g) and crushed 4A molecular sieves (2.5 g). After stirring at room temperature for 3h. diethyl ether (150 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 10% ethyl acetate in hexane as eluent to give the title compound (1.35 g) m.p. 151°-153° C. δ(360 MHz, CDCl3) 4.09 (2H, s, CH2 --C=O). 7.06 (1H, d, J=11.9 Hz, ArCHA =CHBAr), 7.18 (1H, d, J=11.9 Hz, ArCHA =CHBAr), 7.20-7.30 (5H, m, aromatics), 7.50 (1H, dd, J=7.8 and 1.4 Hz, CH=CCl) and 7.86 (1H, dd, J=8.0 and 1.3 Hz, CH=C--C=O). m/e 254 (M+). i.r. (νmax, nujol) 1670 cm-1 (CO). Found: C, 75.1; H, 4.6. C16H11C10 requires: C, 75.4; H, 4.4%.

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 10% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-b7cb5dba06214c57bedf53df799c5827
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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