Pyridine → (9,10-Dihydro-1-phenanthryl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 544690Notes

Reaction equation

HRID 544690 reaction equation
[C:1]1([CH2:15][OH:16])[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:23][C:24]([Cl:34])=[CH:25][C@@H:26]1[C@H:28]([C:29](Cl)=[O:30])[C:27]1([CH3:33])[CH3:32]>C1C=CC=CC=1>[Cl:23][C:24]([Cl:34])=[CH:25][C@@H:26]1[C@H:28]([C:29]([O:16][CH2:15][C:1]2[C:14]3[CH2:13][CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)=[O:30])[C:27]1([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideHCID 132813369,10-Dihydrophenanthrene-1-methanol

Product 1

HCID 86739266(9,10-Dihydro-1-phenanthryl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 9,10-dihydrophenanthrene-1-methanol (0.5 gram, 0.0024 mole) and pyridine (1 gram, 0.013 mole) in benzene (25 ml) was added to a stirred solution of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (0.7 gram, 0.0031 mole) in benzene (25 ml). The mixture was stirred at room temperature for 2.5 days, then partitioned between water (80 ml) and diethyl ether (50 ml). The organic phase was separated and washed consecutively with water, 10% aqueous sodium carbonate and water. The organic phase was then dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to give a yellow oil. The oil was purified by chromatography on silica gel to give (9.10-dihydro-1-phenanthryl)methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate as an oil.

Workup

  1. custompartitioned between water (80 ml) and diethyl ether (50 ml)
  2. customThe organic phase was separated
  3. washwashed consecutively with water, 10% aqueous sodium carbonate and water
  4. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customto give a yellow oil
  8. customThe oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2765f00a4d204bd198de44a7711cff05
Source dataset
uspto-grants-1984_05
Patent number
US04451484

Reaction notes

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