Sodium Hydroxide → HCID 18624185, compound

Temperature

70 °C

A mixture of NaOH (4.9 g), and (Bu)4NI (1 g) in benzene (14 mL) and water (4.9 mL) was heated at 70° C. under argon to obtain a homogeneous mixture. To this mixture was added dropwise a mixture of isobutylaldehyde (10.1 g, 140 mmoles), and the product of Step 1 (25 g, 106 mmoles) in benzene (38 mL). After the addition, the resulting mixture was stirred at 70° C. for 6 h under argon. It was cooled, diluted with water, and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with water, dried (Na2SO4) and concentrated to dryness. This residue was purified by silica gel flash chromatography using 5% EtOAc in hexane. The appropriate fractions (monitored by TLC) were combined and concentrated to dryness to give the desired product (14.9 g, ˜50%). NMR spectrum of the product was consistent for the proposed structure.

1. customto obtain a homogeneous mixture
2. additionTo this mixture was added dropwise
3. additionAfter the addition
4. temperatureIt was cooled
5. extractionextracted with EtOAc (3×150 mL)
6. washThe combined organic extracts were washed with water
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated to dryness
9. customThis residue was purified by silica gel flash chromatography
10. concentrationconcentrated to dryness

ORD record

ord-d82f749d65ac4b02b1f85aecd616f7b7

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06531494B1