Aluminium lithium hydride → (2S,3S)-2,3-bis((2-methylallyl)oxy)butane-1,4-diol

To a solution of (2R,3R)-dimethyl 2,3-bis((2-methylallyl)oxy)succinate (14.7 g, 51.3 mmol) in THF (130 mL) at 0° C. was added slowly a 1.0 M solution of LAH in THF (257 mL, 257 mmol). The mixture was warmed to room temperature and stirred for 2 h, carefully quenched by the addition of EtOAc at 0° C., and then treated with a saturated aqueous solution of potassium sodium tartrate (Rochelle's salt). The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, hexanes/EtOAc gradient) to yield the title compound as a colorless oil (10.87 g, 92%): IR (neat) 3388, 2918, 2880, 1656, 1452, 1046 cm−1; 1H NMR (400 MHz, CDCl3) δ 4.98 (s, 2H), 4.90 (s, 2H), 4.03 (s, 4H), 3.81 (d, J=11.7 Hz, 2H), 3.71 (d, J=11.9 Hz, 2H), 3.64-3.59 (m, 2H), 2.57-2.47 (m, 2H), 1.75 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 142.16, 112.85, 78.75, 74.52, 60.85, 19.68; HRMS-ESI (m/z) [M]+ calcd for C12H22O4, 230.1518; found, 230.1519.

1. customcarefully quenched by the addition of EtOAc at 0° C.
2. additiontreated with a saturated aqueous solution of potassium sodium tartrate (Rochelle's salt)
3. customThe phases were separated
4. extractionthe aqueous layer was extracted with EtOAc
5. washThe combined organic phases were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (SiO2, hexanes/EtOAc gradient)

ORD record

ord-5fdd8db4b5be4290b43e6e0a7e211c0d

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785479B2