Imidazole → 1-(tert-Butyldiphenylsilyl)oxy-dodecan-12-ol

Temperatur

45 °C

In a Schlenk flask, 1,12-Dodecandiol (7.96 g, 39.4 mmol, 1 eq) was dissolved in 40 mL of dry DMF under nitrogen. Imidazole (2.63 g, 38.6 mmol, 1 eq) and tert-butylchlorodiphenylsilane (TBDPS) (10.84 g, 39.4 mmol, 1 eq) were added and the reaction mixture was heated to 45° C. After stirring for 48 h, the reaction was quenched with 300 mL of distilled water. The aqueous phase was extracted four times with diethyl ether, the organic phases were collected and washed twice with 2N HCl (2×100 mL), once with saturated NaHCO3 (200 mL), once with saturated NaCl (200 mL) and dried over Na2SO4. Column-chromatography over silica gel using 10/1 hexane/ethyl acetate as eluent yielded 7.98 g (46%) of the desired product as a slightly yellowish oil. 1H NMR (300.13 MHz): δ (ppm)=1.05 (s, 9H, tert-butyl), 1.26 (br, 16H, —O—CH2—CH2—CH2—CH2—CH2—), 1.58 (m, 4H, —O—CH2—CH2—), 3.65 (m, 4H, —O—CH2—), 7.40 (m, 6H, phenyl), 7.69 (m, 4H, phenyl). 13C NMR (75.48 MHz): δ (ppm)=19.2, 25.7, 25.8, 25.9, 29.3, 29.4, 29.58, 29.6, 32.6, 32.8, 63.1, 64.0, 127.5, 129.4, 134.1, 135.6.

1. customthe reaction was quenched with 300 mL of distilled water
2. extractionThe aqueous phase was extracted four times with diethyl ether
3. customthe organic phases were collected
4. washwashed twice with 2N HCl (2×100 mL), once with saturated NaHCO3 (200 mL), once with saturated NaCl (200 mL)
5. dry with materialdried over Na2SO4

ORD-Eintrag

ord-48e9691f004c47c0a950e9ffd20f0280

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09284411B2