Water → 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propan-1-ol

Step C To a solution of 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester (6 g, 30 mmol) in anhydrous tetrahydrofuran (75 mL) at 0° C. was added a tetrahydrofuran solution (1 M) of LiAlH4 (100 mL, 100 mmol) under nitrogen. The reaction mixture was heated at reflux for 3 h, then cooled to room temperature. Water and aqueous NaOH solution (2N) was added. The mixture was filtered to remove the precipitate, and the filtrate was concentrated. Water was added, and the mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propan-1-ol as a brown oil (4.63 g, 98%).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 3 h
3. filtrationThe mixture was filtered
4. customto remove the precipitate
5. concentrationthe filtrate was concentrated
6. additionWater was added
7. extractionthe mixture was extracted with ethyl acetate
8. customThe organic layer were separated
9. washwashed with water, aqueous HCl solution, brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated

ORD record

ord-01323d4fcc3044d180095c9fe4790432

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354444B2