Tetrahydrofuran → HCID 69527272, compound

HRID 1862188Notes

Reaction equation

HRID 1862188 reaction equation
[CH3:1][P:2]([CH3:4])[CH3:3].C([CH:7]([Br:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=C.O1CC[CH2:17][CH2:16]1>C(OCC)C>[Br-:14].[CH:16]([CH2:1][P+:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])[CH3:3])=[CH2:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 68983TrimethylphosphineHCID 15361356(1-Bromoprop-2-en-1-yl)benzene

Product 1

HCID 69527272HCID 69527272, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trimethylphosphine (50.0 ml of a 1.0 molar solution in tetrahydrofuran, 5.00×10−2 mol) was added via addition funnel over about 2 minutes into a thoroughly nitrogen degassed dispersion of vinylbenzyl bromide (9.85 g, 5.00×10−2 mol) in diethyl ether (100 ml). A solid precipitate began to form almost immediately. The reaction was allowed to stir for 4 hours at room temperature, then was placed in a freezer overnight. The solid product was isolated by filtration, washed three times with 100 ml of diethyl ether, and dried under vacuum for 2 hours. Pure product (11.22 g) was recovered as a white powder (82.20% yield).

Workup

  1. customto form almost immediately
  2. waitwas placed in a freezer overnight
  3. customThe solid product was isolated by filtration
  4. washwashed three times with 100 ml of diethyl ether
  5. customdried under vacuum for 2 hours

Sources & evidence

ORD record
ord-563e094d942347f9aae646ff93b45f44
Source dataset
uspto-grants-2003_03
Patent number
US06537730B1

Reaction notes

Loading…