Hexanal → HCID 24776469, compound

To a solution of (3-bromo-3,3-difluoro-prop-1-ynyl)-triisopropyl-silane (156 mg, 0.5 mmol) and hexanal (60 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 h and quenched with 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 (82 mg, 65%) as colorless liquid. Colorless liquid, yield: 78%. IR (neat): 3320, 2934, 2261, 1223, 1096 cm−1. 1H NMR (500 MHz, CDCl3) δ 4.49-4.52 (m, 1H), 2.14 (bs, 1H), 1.74-1.77 (m, 2H), 1.45-1.47 (m, 2H), 1.33-1.38 (m, 4H), 0.91 (t, J=6.5 Hz, 3H); 19F NMR (470 MHz, CDCl3) δ −32.9 (s, 2F); 13C NMR (125 MHz, CDCl3) δ 101.5 (t, J=288 Hz), 91.5 (t, J=5.8 Hz), 77.3 (t, J=38 Hz), 62.2, 36.8, 31.4, 24.6, 22.6, 14.1; GCMS: 157, 137, 115, 104, 91.

1. additionAfter the addition
2. customquenched with 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-f7ad66fb21c7405687bd8b741a0012cf

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703829B2