Butanal → HCID 86657764, compound

HRID 2067953Notes

Reaction equation

HRID 2067953 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH:8](=O)[CH2:9][CH2:10][CH3:11].O>ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:8](=[N:7][S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 261ButanalHCID 962WaterHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 86657764HCID 86657764, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-2-methyl-propane-2-sulfinamide (6.7 g, 55 mmol) in dichloromethane (125 mL) is added butyraldehyde (4.0 g, 55 mmol) followed by titanium isopropoxide (32 g, 110 mmol). The reaction is then heated at reflux (bath temperature=60° C.) for 4 hours. The resultant mixture is cooled to room temperature and poured into a stirred mixture of diatomaceous earth (10 g) and water (100 mL). The slurry is stirred for 10 min and then filtered. The organic layer from the filtrate is concentrated in vacuo to afford a crude yellow oil which is purified by flash chromatography on silica gel (eluted with 5 to 30% dioxane/hexanes) to afford (S)-2-methyl-propane-2-sulfinic acid butylideneamide as a colorless oil (7.4 g, 77%).

Workup

  1. temperatureThe reaction is then heated
  2. filtrationfiltered
  3. concentrationThe organic layer from the filtrate is concentrated in vacuo
  4. customto afford a crude yellow oil which
  5. customis purified by flash chromatography on silica gel (eluted with 5 to 30% dioxane/hexanes)

Sources & evidence

ORD record
ord-bdc0ea9a12694fdb98cd3f7b7f27d815
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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