Propanal → HCID 54326900, compound

HRID 886607Notes

Reaction equation

HRID 886607 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:29]([Li])[CH2:30][CH2:31]C.C(=O)CC.CCCCCC>C1COCC1>[Br:2][C:3]1[CH:28]=[CH:27][CH:26]=[C:5]([CH:6]=[CH:29][CH2:30][CH3:31])[CH:4]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 8058HexaneHCID 17794920HCID 17794920, compoundHCID 178418339Butyllithium

Product 1

HCID 54326900HCID 54326900, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (3-bromo-benzyl)-triphenyl-phosphonium chloride (10 g, 23.2 mmol) in THF (100 mL) at 0° C. was added n-butyl lithium (10.2 mL, 2.5 N in hexane, 25.5 mmol) dropwise. The resulting orange suspension was stirred for 30 minutes. Propanal (1.61 g, 28 mmol) was added and the resulting mixture was stirred at room temperature for 2 hours. The mixture was cooled to 0° C. and cold hexane (500 mL) was added. The white precipitate was filtered, and the filtrate was concentrated. The residue was purified with flash chromatography using hexane to afford 1-bromo-3-but-1-enyl-benzene (4.4 g, 90%) as a mixture of 3:1 (E):(Z) isomers. MS: m/z 211 (M+H+). The mixture was distillled under vacuum to afford the (E) isomer (1 g, >95% E) and the (Z) isomer (200 mg, 75% Z).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. filtrationThe white precipitate was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-e02f2e03e6924a6d96d7b232729b548d
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

Loading…