2-Bromopropene → HCID 534462, compound

HRID 2058133Notes

Reaction equation

HRID 2058133 reaction equation
[Br:1][C:2]([CH3:4])=[CH2:3].[Mg:5].[CH2:6]=[C:7]([CH:12]=[CH2:13])[CH2:8][CH2:9][CH:10]=[O:11].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([Mg:5][Br:1])[CH:7]=[CH2:6].[CH3:4][C:2]([CH:10]([OH:11])[CH2:9][CH2:8][C:7](=[CH2:6])[CH:12]=[CH2:13])=[CH2:3]

Participants

7

Reactant 4

HCID 112022-BromopropeneHCID 25517Ammonium ChlorideHCID 548982HCID 548982, compoundHCID 5462224Magnesium

Product 2

HCID 534462HCID 534462, compoundYield 74.7%HCID 178455850HCID 178455850, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Propenyl magnesium bromide is prepared under nitrogen from 2-bromopropene (50 g, 0.417 M) and magnesium (12 g, 0.5 M) in tetrahydrofuran (150 ml) in the usual manner. To this reagent, a solution of 4-methylene-5-hexenal (62 g, 0.564 M) in tetrahydrofuran (100 ml) is slowly added during a two hour period at 0° C. After the addition is complete, the mixture is allowed to warm to room temperature and then stirred overnight. The resulting mixture is poured into cold saturated ammonium chloride solution (500 ml) and the aqueous layer is extracted with ether (3×500 ml). The combined organic layers are dried (Na2SO4) and the solvent is removed in vacuo. The residue (56.5 g) is purified by column chromatography on silica gel (350 g) with 25% ether in petroleum ether to give 2-methyl-6-methylene-1,7-octadien-3-ol (32 g, 51%) as a colorless liquid.

Workup

  1. additionAfter the addition
  2. extractionthe aqueous layer is extracted with ether (3×500 ml)
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. customthe solvent is removed in vacuo
  5. customThe residue (56.5 g) is purified by column chromatography on silica gel (350 g) with 25% ether in petroleum ether

Sources & evidence

ORD record
ord-e5e2bc33b52d4bdd841e12d351fec8f6
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

Loading…