3-Isopropylbenzaldehyde → HCID 89252079, compound

HRID 1851961Notes

Reaction equation

HRID 1851961 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([CH3:3])[CH3:2].[CH3:12][C:13]([S@@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)/[CH:7]=[N:18]/[S@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5206803-IsopropylbenzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89252079HCID 89252079, compound

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isopropylbenzaldehyde (0.711 g, 4.75 mmol) in THF (5 mL) was added (S)-2-methyl-2-propanesulfinamide (0.534 g, 4.32 mmol) and Ti(OiPr)4 (2.75 mL, 8.64 mmol). The resulting mixture was allowed to stir over night at rt where it was then quenched with aqueous NH4Cl (5 mL) and diluted with EtOAc (100 mL). The mixture was then filtered through celite using excess EtOAc to rinse, concentrated to an oil crude and separated by silica gel (EtOAc:Hexanes) to isolate the title compound.

Workup

  1. customwas then quenched with aqueous NH4Cl (5 mL)
  2. additiondiluted with EtOAc (100 mL)
  3. filtrationThe mixture was then filtered through celite
  4. washto rinse
  5. concentrationconcentrated to an oil crude
  6. customseparated by silica gel (EtOAc:Hexanes)

Sources & evidence

ORD record
ord-0a35f03d56d743f1a3abda20a37eda24
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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