Pivalaldehyde → HCID 24873309, compound

To a solution of (3-bromo-3,3-difluoro-prop-1-ynyl)-triisopropyl-silane (156 mg, 0.5 mmol) and 2,2-dimethyl-propionaldehyde (52 mg, 0.6 mmol) in THF (5 mL), TBAF (1M, 0.75 mL) was added dropwise at −90° C. After the addition was completed, the reaction mixture was stirred for 0.5 hour and quenched saturated aq. NH4Cl. The mixture was extracted with ether (20 mL×3) and washed with water (20 mL×2). After drying over Na2SO4 the solvent was removed and the product was purified by silica gel chromatography (AcOEt:hexane=1:20) to afford the title compound as a colorless liquid. 1H NMR (500 MHz, CDCl3) δ 4.08-4.09 (m, 1H), 1.83 (d, J=6.0 Hz, 1H), 0.965 (s, 9H).

1. additionAfter the addition
2. customquenched saturated aq. NH4Cl
3. extractionThe mixture was extracted with ether (20 mL×3)
4. washwashed with water (20 mL×2)
5. dry with materialAfter drying over Na2SO4 the solvent
6. customwas removed
7. customthe product was purified by silica gel chromatography (AcOEt:hexane=1:20)

ORD record

ord-4f90846b28284571ba80c2033a0f6d91

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703829B2