Water → 2,2-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol

To solution of LiAlH4 (397 mL, 397 mmol) in THF (250 mL) cooled in an ice bath to 0° C. was added methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate (82 g, 378 mmol) in THF (250 mL) via addition funnel keeping the internal temperature below 6° C. When addition was complete the reaction was allowed to warm to room temperature and stir overnight. The mixture was cooled in an ice bath and quenched with H2O (16 mL, 888 mmol), then after 5 minutes, 10 N NaOH (16 mL, 160 mmol), and after another 15 minutes, H2O (48 mL, 2664 mmol). The mixture was allowed to stir for 30 minutes, then filtered with a THF rinse. The filtrate was concentrated and azeotropically dried with toluene. Further drying under vacuum gave 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol as a colorless liquid: 1H NMR (400 MHz, CDCl3) δ 4.58 (m, 1H), 3.85 (m, 1H), 3.6 (d, 1H), 3.5 (m, 2H), 3.4 (m, 1H), 3.2 (d, 1H), 2.8 (t, 1H), 1.8 (m, 2H), 1.6 (m, 4H), 0.85 (s, 6H).

1. additionvia addition funnel
2. customthe internal temperature below 6° C
3. additionWhen addition
4. temperatureThe mixture was cooled in an ice bath
5. waitafter 5 minutes
6. stirringto stir for 30 minutes
7. filtrationfiltered with a THF
8. washrinse
9. concentrationThe filtrate was concentrated
10. dry with materialazeotropically dried with toluene
11. customFurther drying under vacuum

ORD record

ord-7a9d9b1929184d7c81860d6b000868fd

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513234B2