Toluene → 13-Oxabicyclo[10.1.0]tridecane

HRID 2170239Notes

Reaction equation

HRID 2170239 reaction equation
[CH2:1]1[O:9][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[SiH](CC)(CC)CC.[C:17]1(C)[CH:22]=CC=[CH:19][CH:18]=1>>[CH:2]12[O:9][CH:1]1[CH2:22][CH2:17][CH2:18][CH2:19][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:3]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 7276Styrene OxideHCID 12052Triethylsilane

Product 1

HCID 924813-Oxabicyclo[10.1.0]tridecane

Conditions

Temperature
90 °C

Procedure

The preparation of reaction mixtures is conducted under an inert atmosphere, for example, in a nitrogen-filled dry box. 70 mg (0.38 mmol) styrene oxide, 88 mg (0.76 mmol) Et3SiH and 20 mg (0.018 mmol) of the catalyst [Ni(NPtBu3)]4 are dissolved in 6 mL toluene. The solution is transferred into a Teflon-sealed glass reactor equipped with a Teflon-sealed magnetic stir bar. The reaction mixture is then stirred at 1200 rotations per minute (rpm) for 12 hours in an oil bath at 90° C.

Workup

  1. customThe preparation of reaction mixtures
  2. additionfilled
  3. customdry box
  4. customsealed glass reactor
  5. customsealed magnetic stir bar

Sources & evidence

ORD record
ord-589b58294dc541ec8c6b4498b682a37c
Source dataset
uspto-grants-2015_06
Patent number
US09051229B2

Reaction notes

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