Dimethyl Sulfoxide → 5-Tert-butylpyridine-3-carbaldehyde

Oxalyl chloride (158 μL, 1.819 mmol) in methylene chloride (10 mL) was placed in a two-necked flask at −78° C., followed by the addition of dimethyl sulfoxide (129 μL, 1.819 mmol). Stirring was continued for 20 min, followed by addition of (5-tert-butylpyridin-3-yl)methanol (0.2 g, 1.21 mmol) in methylene chloride (10 mL). After the mixture was stirred at −78° C. for additional 20 min, triethylamine (0.59 mL, 4.24 mmol) was added. The cooling bath was removed and the suspension was allowed to warm to room temperature. Water (50 mL) was added, the yellow organic layer was separated, and the aqueous layer was extracted with methylene chloride (3×30 mL). The combined organic solution was dried and concentrated to give 5-tert-butylnicotinaldehyde as an orange-yellow liquid which was used directly for next step without further purification.

1. stirringAfter the mixture was stirred at −78° C. for additional 20 min
2. customThe cooling bath was removed
3. additionWater (50 mL) was added
4. customthe yellow organic layer was separated
5. extractionthe aqueous layer was extracted with methylene chloride (3×30 mL)
6. customThe combined organic solution was dried
7. concentrationconcentrated

ORD record

ord-c057b322682f44368de96eb2ed4d5f3f

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2