tert-Butyl (triphenylphosphoranylidene) acetate → HCID 131734210, compound

HRID 1497528Notes

Reaction equation

HRID 1497528 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH:11]=O.C1(P(=[CH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10]/[CH:11]=[CH:32]/[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 55274760HCID 55274760, compound

Product 1

HCID 131734210HCID 131734210, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2-chloro-4-methoxyphenyl)acetaldehyde (1.22 g) in toluene (30.0 mL) was added tert-butyl (triphenylphosphoranylidene)acetate (2.75 g), followed by stirring at 80° C. overnight. The reaction mixture was air-cooled to room temperature, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl (2E)-4-(2-chloro-4-methoxyphenyl)but-2-enoate (1.67 g).

Workup

  1. temperatureThe reaction mixture was air-cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cc4a1e33b650413c83bfc8add351e180
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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