Methanol → HCID 14059378, compound

To a solution of ethyl 4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanoate (11.3 g, 43.7 mmol) in toluene (300 mL) cooled to −78° C. under nitrogen was added diisobutylaluminum hydride 1.0M in heptane (53 mL, 52.5 mmol) slowly, keeping the internal temperature below −70° C. The mixture was allowed to stir in the cold for 15 minutes (TLC: 20% EtOAc in hexane). The reaction was quenched with MeOH (3.00 mL, 161 mmol) allowed to warm to −10 C, diluted with 500 mL of ethyl acetate and 500 mL of saturated NaCl. The mixture was allowed to warm and stir for 60 minutes forming a gel. The gelatinous mixture was filtered through diatomaceous earth and washed with 750 mL of ethyl acetate. The organic layer was separated, dried over MgSO4 and concentrated. Drying under vacuum gave 4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanal as a clear oil: 1H NMR (400 MHz, CDCl3) δ 9.8 (s, 1H), 4.6 (t, 1H), 3.8 (m, 1H), 3.6 (m, 1H), 3.5 (d, 1H), 3.0, (d, 1H), 2.4 (m, 2H), 1.8 (m, 1H), 1.7-1.5 (m, 6H), 0.93 (s, 3H), 0.92 (s, 3H).

1. customthe internal temperature below −70° C
2. temperatureto warm to −10 C
3. temperatureto warm
4. customforming a gel
5. filtrationThe gelatinous mixture was filtered through diatomaceous earth
6. washwashed with 750 mL of ethyl acetate
7. customThe organic layer was separated
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customDrying under vacuum

ORD record

ord-15ed855f23f44f5180c48f97fb2d3098

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513234B2