Styrene Oxide → HCID 14391220, compound

HRID 1381534Notes

Reaction equation

HRID 1381534 reaction equation
[CH2:1]1[O:9][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([NH2:16])[CH:11]1[O:15][CH2:14][CH2:13][CH2:12]1>CO>[O:15]1[CH2:14][CH2:13][CH2:12][CH:11]1[CH2:10][NH:16][CH2:1][CH:2]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:9]

Participants

4

Reactant 2

HCID 7276Styrene OxideHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 14391220HCID 14391220, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of styrene oxide (1.20 g, 0.010 mole) and tetrahydrofurfurylamine (4.05 g, 0.040 mole) was heated on a steam bath for 2 hours. After standing at ambient temperature for 60 hours the reaction mixture was dissolved in 10 ml of methanol and the solution poured into 120 ml of ice-water. The aqueous mixture was extracted with methylene chloride (50 ml). The extract was dried (over magnesium sulfate) and concentrated to give an oil which began to solidify within one hour. The material was triturated with petroleum ether to obtain 0.73 g of an off-white solid (33%). The solid was recrystallized from isooctane; m.p. 70°-72° C.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. extractionThe aqueous mixture was extracted with methylene chloride (50 ml)
  3. dry with materialThe extract was dried (over magnesium sulfate)
  4. concentrationconcentrated
  5. customto give an oil which
  6. waitto solidify within one hour
  7. customThe material was triturated with petroleum ether

Sources & evidence

ORD record
ord-265a9c5401274cc1837ba7b7cb1c424c
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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