Diisobutylaluminum hydride → 2-((t-Butyldimethylsilyloxy)methyl)-but-2-ene-1,4-diol

Temperature

78 °C

A 2.210 g (9.69 mmol) sample of 3-((t-butyldimethylsilyloxy)methyl)-4-hydroxybut-2-eneoic acid, 1,4-lactone, from Example 336A, was dissolved in 6 mL of methylene chloride, cooled in a dry ice bath, and 14.2 mL (21.3 mmol) of DIBAL was added. The mixture was stirred at 78° C. for 4 hours, allowed to warm to room temperature and stirred for 16 hours. The mixture was cooled to -78° C. and quenched with 1.53 mL of methanol and 2.55 mL of water. The mixture was filtered, and the filtrate concentrated and chromatographed on silica gel, eluting with 50% and 90% ethyl acetate in hexane. The solvent was removed and the product dried to afford 1.055 g of the title product, which was taken directly to the next step.

1. temperaturecooled in a dry ice bath
2. temperatureto warm to room temperature
3. stirringstirred for 16 hours
4. temperatureThe mixture was cooled to -78° C.
5. customquenched with 1.53 mL of methanol and 2.55 mL of water
6. filtrationThe mixture was filtered
7. concentrationthe filtrate concentrated
8. customchromatographed on silica gel
9. washeluting with 50% and 90% ethyl acetate in hexane
10. customThe solvent was removed
11. customthe product dried

ORD record

ord-7108dc8711f5437b86ec96b5c061f6b0

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05616714