Tetrahydrofuran → HCID 18512089, compound

Temperature

0 °C

The product from Example 53A (6.42 g, 36.5 mmoles) in anhydrous THF (50 mL) was treated with diisobutylaluminum hydride (DIBAL) (37.0 mL, 37.0 mmoles, 1.0M in hexanes) dropwise at −78° C. After 30 minutes, an additional portion of DIBAL (37.0 mL) was added dropwise. After an additional 30 minutes, the acetone/dry ice bath was removed, and the reaction mixture was warmed to 0° C. After an additional 30 minutes, the reaction was carefully quenched with saturated NH4Cl. The mixture was diluted with diethyl ether (200 mL) and saturated sodium potassium tartrate (250 mL) and stirred vigorously for 2.0 hours. The two phases were separated, and the organic phase was washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound with no further purification. MS (DCI) m/z 181 (M+H)+.

1. waitAfter an additional 30 minutes
2. customthe acetone/dry ice bath was removed
3. waitAfter an additional 30 minutes
4. customthe reaction was carefully quenched with saturated NH4Cl
5. additionThe mixture was diluted with diethyl ether (200 mL) and saturated sodium potassium tartrate (250 mL)
6. customThe two phases were separated
7. washthe organic phase was washed with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-95d2a91e07ce448ab99ba7863a64acfa

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06583180B2