Styrene → HCID 69585507, compound

HRID 1682165Notes

Reaction equation

HRID 1682165 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+](=[CH:11][C:12]([O:14][C:15]1([CH3:24])[CH2:20][CH2:19][CH:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]1)=[O:13])=[N-]>ClCCl>[C:3]1([CH:2]2[CH2:1][CH:11]2[C:12]([O:14][C:15]2([CH3:24])[CH2:20][CH2:19][CH:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]2)=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7501StyreneHCID 86746438HCID 86746438, compound

Product 1

HCID 69585507HCID 69585507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of styrene (1.063 g, 10.2 mmol) and Rh2 (4R-BNOX)4 (0.0050 g, 0.0058 mmol) in 3.0 mL of refluxing anhydrous dichloromethane was added, by syringe at room temperature, 1-menthyl diazoacetate (0.109 g, 0.485 mmol) in 3.0 mL of dichloromethane under nitrogen and at an addition rate of 0.8 mL/h (syringe pump). After addition was complete, the dichloromethane solution was passed through a plug of neutral alumina, and solvent was removed under reduced pressure. The residue was analyzed by capillary gas chromatography (SPB-5 column) for diastereomeric separation and enantiomeric purity. Similar procedures were followed for the cyclopropanation of 3,3-dimethyl-1-butene, ethyl vinyl ether, and dihydropyran.

Workup

  1. additionwas added, by syringe at room temperature
  2. additionAfter addition
  3. customwas removed under reduced pressure
  4. customThe residue was analyzed by capillary gas chromatography (SPB-5 column) for diastereomeric separation and enantiomeric purity

Sources & evidence

ORD record
ord-038c7227f6424dbca1f3b22dab9f7540
Source dataset
uspto-grants-1992_12
Patent number
US05175311

Reaction notes

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