((2S,3R)-3-Undecyloxiran-2-yl)methanol → (R)-1,3-dihydroxytetradecane

Temperature

0 °C

To a solution of epoxide 8 (9.00 g, 40 mmol) in tetrahydrofuran (80 mL) at -20° C. was added a solution of Red-Al (40 mL, 3M) and the reaction temperature was slowly raised to 0° C. and subsequently to room temperature and stirred for 12 h. After completion of the reaction (TLC), the excess of Red-Al was quenched with methanol (10 mL) and poured in to a conical flask containing ethyl acetate (400 mL) and rochelle salt solution (100 mL) and stirred for 2 h until clear separation of two layers occurred. The organic layer was separated, dried and concentrated to give the diol 9 as a colorless solid (8.1 g, 89%). m.p. 59°-60° C.

1. customAfter completion of the reaction (TLC)
2. customthe excess of Red-Al was quenched with methanol (10 mL)
3. additionpoured in to a conical flask
4. additioncontaining ethyl acetate (400 mL) and rochelle salt solution (100 mL)
5. stirringstirred for 2 h until clear separation of two layers
6. customThe organic layer was separated
7. customdried
8. concentrationconcentrated

ORD record

ord-9bd9a246afc1474c8cbb4f19b3d10e65

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05593969