Diethyl Ether → HCID 54502162, compound

HRID 1651064Notes

Reaction equation

HRID 1651064 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([OH:16])=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:4]=2[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[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 67796250HCID 67796250, compound

Product 1

HCID 54502162HCID 54502162, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-5-hydroxy-dibenzo[a,e]cyclooctene (1.5 g) in dry dichloromethane (60 ml) was added pyridinium dichromate (5 g) and crushed 4 A molecular sieves (2.5 g). After stirring at room temperature for 14 h, 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 5% ethyl acetate in hexane as eluent to give. as a colourless oil, the title compound (1.4 g). δ (360 MHz, CDCl3) 4.04 (2H. s, CH2), 6.93 (1H, d, J =12.9 Hz, CHA =CHB), 7.10 (1H. d, J=12.9 Hz, CHA =CHB), 7.22-7.42 (6H, m, ArH), 8.17 (1H. d, J =8.4 Hz, ClC=CH--CH=C--C=O). m/e 256 and 254 (M+).

Workup

  1. customcrushed 4 A molecular sieves (2.5 g)
  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

Sources & evidence

ORD record
ord-aea8e99721974d47ba5d75e714c41066
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

Loading…