Pyridine → (+)-4-Phenyl-2-indanyl (+)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 905381Notes

Reaction equation

HRID 905381 reaction equation
[Br:1][C:2]([Br:12])=[CH:3][C@@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C:13]1([C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH:22]([OH:28])[CH2:23]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.C1(C)C=CC=CC=1>O>[Br:1][C:2]([Br:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:28][CH:22]2[CH2:21][C:20]3[C:24](=[CH:25][CH:26]=[CH:27][C:19]=3[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:23]2)=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-olHCID 86738410(+)-cis-3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86738411(+)-4-Phenyl-2-indanyl (+)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a manner similar to Example 12A, the reaction of 0.51 g (0.0016 mole) of (+)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (an additional four drops were added 1 hour after original addition) with 0.33 g (0.0016 mole) of (+)-4-phenyl-2-indanol (EE 50%), 0.16 g (0.002 mole) of pyridine and toluene produced an oil. The oil was subjected to vacuum column chromatography, whereby the oil was placed on silica gel packed in a sintered glass suction funnel, and the eluant was drawn through by water aspirator vacuum. Elution was accomplished with hexane, then 24:1 hexane/ethyl acetate to give (+)-4-phenyl-2-indanyl (+)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate as an oil, EE 50% (alcohol moiety). The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionwere added 1 hour
  2. customproduced an oil
  3. custompacked in a sintered glass suction funnel
  4. washElution

Sources & evidence

ORD record
ord-dc875c18c8e74842bc3e8521020a5747
Source dataset
uspto-grants-1983_12
Patent number
US04423255

Reaction notes

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