Diisobutylaluminum hydride → 3-(4-Methoxyphenyl)propanal

A solution of ester 12d (0.8346 g, 4.3 mmol) in 15 mL dry CH2Cl2 was cooled to -78° C. and treated with DIBAL (1.0M solution in dry CH2Cl2, 4.3 mL, 4.3 mmol, 1.0 equiv), upon completion by tlc the reaction was quenched immediately with 4.0 mL dry CH3OH. The reaction mixture was diluted with 15 mL saturated aqueous sodium potassium tartrate and warmed gradually to room temperature, partitioned, and extracted with CH2Cl2 (3×20 mL). The combined extracts were washed with saturated aqueous sodium potassium tartrate (3×25 mL), dried (MgSO4), filtered and concentrated in vacuo. SGC chromatotron (SiO2, 4 mm, 20-35% EtOAc/hexanes) afforded 13d (0.702 g, 0.706 g theoretical, 99%). For 13d: 1H NMR (CDCl3, 250 MHz) d 9.78 (d, 1H, J=1.4 Hz, CHO), 7.09 (d, 2H, J=8.6 Hz, Ar C2-H and C6-H), 6.82 (d, 2H, J=8.6 Hz, Ar C3-H and C5-H), 3.76 (s, 3H, OCH3), 2.87 (dd, 2H, J=6.9, 8.3 Hz, ArCH2), 2.72 (ddd, 2H, J=1.4, 6.9, 8.3 Hz, CH2 (C=O)); 13C NMR (CDCl3, 125 MHz) d 201.7, 158.0, 132.3, 129.1, 113.9, 55.1, 45.4, 27.2; IR (neat) nmax 2935, 2835, 1722, 1611, 1583, 1513, 1464, 1442, 1301, 1247, 1178, 1034, 831 cm-1. See FIG. 18h.

1. customwas quenched immediately with 4.0 mL dry CH3OH
2. additionThe reaction mixture was diluted with 15 mL saturated aqueous sodium potassium tartrate
3. custompartitioned
4. extractionextracted with CH2Cl2 (3×20 mL)
5. washThe combined extracts were washed with saturated aqueous sodium potassium tartrate (3×25 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-afea663760844b0eb7ca0f54f524861f

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05939268