Iodine → HCID 66851827, compound

To a solution of 3,3-dimethylbutanal (Aldrich) (3.99 g, 39.8 mmol) in of acetonitrile (40 mL) was added 4 g of molecular sieves (4A beads, 8-12 mesh) and 2,2-dimethylpropan-1-amine (Aldrich) (3.16 g, 36.2 mmol). The mixture was stirred for 12 h at room temperature. The mixture was filtered and to the filtrate was successively added potassium thiocyanate (4.68 g, 48.1 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (1.24 g, 4.71 mmol). The temperature was adjusted at 50° C. and the mixture was stirred until all solids were dissolved then iodine (18.4 g, 72.4 mmol) was added. The reaction was stirred at 50° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with EtOAc. The solution was washed with a solution of sodium metabisulfate. The aqueous layers was brought to pH=9 by adding NaOH (25%) and extracted with EtOAc. The Organic extracts were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was crystallized from EtOAc/Hexane to give 4.9 g of the title compound. MS (ESI+) m/z 227 (M+H)+.

1. filtrationThe mixture was filtered and to the filtrate
2. customwas adjusted at 50° C.
3. stirringthe mixture was stirred until all solids
4. dissolutionwere dissolved
5. stirringThe reaction was stirred at 50° C. for 12 h
6. temperatureThe reaction mixture was cooled to room temperature
7. washThe solution was washed with a solution of sodium metabisulfate
8. additionby adding NaOH (25%)
9. extractionextracted with EtOAc
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe residue was crystallized from EtOAc/Hexane

ORD record

ord-3efc94d5f54d45ad9294e2bbd99c6019

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875640B2