Lithium borohydride → HCID 58550743, compound

Methyl 3-formyl-4-isopropoxy-benzoate (180 mg, 0.8 mmol) was dissolved in tetrahydrofuran (5 mL) and lithium borohydride (35 mg, 1.6 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes, then quenched with methanol (3 mL). The reaction mixture was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate (3 mL) and extracted with ethyl acetate (3×10 mL). The organic layers were washed with brine solution (1×10 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield methyl 3-(hydroxymethyl)-4-isopropoxy-benzoate (180 mg, 99%) as a viscous liquid. ESI-MS m/z calc. 224.3. found 225.3 (M+1)+; Retention time: 1.26 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 8.09 (s, 1H), 7.89 (d, J=8.6 Hz, 1H), 7.13 (d, J=8.6 Hz, 1H), 5.25 (t, J=5.6 Hz, 1H), 4.86-4.68 (m, 1H), 4.54 (d, J=5.6 Hz, 2H), 3.87 (s, 3H), 1.35 (d, J=6.0 Hz, 6H).

1. customquenched with methanol (3 mL)
2. additionThe reaction mixture was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate (3 mL)
3. extractionextracted with ethyl acetate (3×10 mL)
4. washThe organic layers were washed with brine solution (1×10 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-59da9e14c4fe46d693acd197ee916bab

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181273B2