(R,R)-Stilbene oxide → HCID 14391217, compound

HRID 1681344Notes

Reaction equation

HRID 1681344 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[CH2:16]([NH2:22])[CH:17]1[O:21][CH2:20][CH2:19][CH2:18]1>O>[C:10]1([CH:8]([OH:9])[CH:7]([NH:22][CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][O:21]2)[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 185583(R,R)-Stilbene oxideHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 14391217HCID 14391217, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of trans-stilbene oxide (1.96 g, 0.010 mol) and tetrahydrofurfurylamine (3.03 g, 0.030 mol) was heated at 140° C. for 2 hours. After standing at ambient temperature for 18 hours the mixture was diluted with water (150 mL). An oil separated from the solution but solidified on standing for an hour. NMR and mass spectral analyses showed stilbene oxide remaining. The solid was treated with another 3.03 g of tetrahydrofurfurylamine and the mixture heated at 150° C. for another 3 hours. The reaction mixture was treated with water (150 mL) as before to obtain 2.28 g (77%) of an off-white solid after drying under ambient conditions for 18 hours. The solid was recrystallized form toluene; mp 167°-168° C.

Workup

  1. customAn oil separated from the solution
  2. waiton standing for an hour
  3. additionThe solid was treated with another 3.03 g of tetrahydrofurfurylamine
  4. temperaturethe mixture heated at 150° C. for another 3 hours
  5. additionThe reaction mixture was treated with water (150 mL) as before

Sources & evidence

ORD record
ord-2cdc210df03c49af9f8e1645ddc1288f
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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