Triethylamine → HCID 59805529, compound

To a solution of hex-5-en-1-ol (20.0 g, 200 mmol) in CH2Cl2 (350 mL, 0.57 M) at 0° C. was added triethylamine (33.7 mL, 240 mmol, 1.2 equiv), DMAP (1.22 g, 10 mmol, 0.05 equiv) and then 4-Nitrobenzoyl chloride (39 g, 210 mmol, 1.05 equiv.). The reaction was stirred at rt for 2 h. The reaction mixture was quenched with a saturated NH4Cl solution and extracted 3 times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The product was purified by combi-flash 2×120 g silica gel cartridge using gradient (0-5% in 5 min, 5-25% in 30 min, 25-40% EA/Hex in 10 min) to afford the desired product (35 g, Yield=70%) as a yellowish oil. 1H NMR (500 MHz, acetone-d6): δ 8.36 (d, 2H), 8.26 (d, 2H), 5.87-5.79 (m, 1H), 5.03 (d, 1H), 4.94 (d, 1H), 4.38 (t, 2H), 2.14 (m, 2H), 1.84-1.78 (m, 2H), 1.60-1.54 (m, 2H).

1. customThe reaction mixture was quenched with a saturated NH4Cl solution
2. extractionextracted 3 times with CH2Cl2
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated
7. customThe product was purified by combi-flash 2×120 g silica gel cartridge
8. custom(0-5% in 5 min, 5-25% in 30 min, 25-40% EA/Hex in 10 min)

ORD record

ord-b2e55df795bb4cfb9cbd23d01ec44c47

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622502B2