Water → 4-Allyl-1-ethoxymethoxy-2-ethylbenzene

HRID 970832Notes

Reaction equation

HRID 970832 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH2:11][CH3:12])=[C:4]([CH2:13][CH3:14])[CH:3]=1.[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17].O>CN(C=O)C.Cl[Pd](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH2:11][CH3:12])=[C:4]([CH2:13][CH3:14])[CH:3]=1)[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 962WaterHCID 90628AllyltributylstannaneHCID 179831144-Bromo-1-ethoxymethoxy-2-ethylbenzene

Product 1

HCID 179830474-Allyl-1-ethoxymethoxy-2-ethylbenzene

Reagents, catalysts & solvents 2

HCID 178479802HCID 178479802, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

15 g (58 mmol) of 4-bromo-1-ethoxymethoxy-2-ethylbenzene are dissolved in 150 ml of DMF. 26.9 ml (87 mmol) of allyltributyltin are added, and then the mixture is degassed with a nitrogen stream. 1.2 g (1.8 mmol) of dichlorobis (triphenylphosphino)palladium are added, and the medium is heated at 120° C. for 10 hours. The reaction medium is poured into water, and then extracted with ethyl acetate. The residue obtained after drying and concentration is purified by chromatography on a silica column (eluent heptane, and then heptane 95/ethyl acetate 5). A yellow oil is obtained (m=13.6 g, y=100%).

Workup

  1. customthe mixture is degassed with a nitrogen stream
  2. extractionextracted with ethyl acetate
  3. customThe residue obtained
  4. customafter drying
  5. concentrationconcentration
  6. customis purified by chromatography on a silica column (eluent heptane
  7. customA yellow oil is obtained (m=13.6 g, y=100%)

Sources & evidence

ORD record
ord-d5e7f628861b4b65825e5f028e8db75f
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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