Hydrochloric Acid → HCID 68505968, compound

Temperature

40 °C

The solution of 2.0 g of 2-triisopropylsilanyloxyethyl 4-methyl-3-(2-triisopropylsilanyloxyethoxy)benzoate in 6 ml of tetrahydrofuran is added dropwise at 20-40° C. to the stirred mixture of 0.149 g of lithium aluminium hydride in 6 ml of tetrahydrofuran. The reaction mixture is stirred at 40° C. over 4 hours and subsequently cooled to room temperature. 0.6 ml of water, 0.6 ml of 2N NaOH and once again 0.6 ml of water are added dropwise successively and the suspension is stirred at room temperature over 1 hour. The reaction mixture is poured onto 100 ml of 2N HCl (cold) and extracted with ethyl acetate (2×100 ml). The organic phases are washed successively with 2N HCl (100 ml), water (100 ml) and brine (1×100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.71 (1:1 EtOAc-heptane); Rt=6.30.

1. temperaturesubsequently cooled to room temperature
2. stirringthe suspension is stirred at room temperature over 1 hour
3. extractionextracted with ethyl acetate (2×100 ml)
4. washThe organic phases are washed successively with 2N HCl (100 ml), water (100 ml) and brine (1×100 ml)
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated by evaporation

ORD record

ord-bbb3b7edfe154209be846126749ae83e

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842688B2