Chloroform → HCID 9994068, compound

To a 100 mL 2-necked round bottom flask equipped with a septurn and nitrogen inlet was added 3.0 g (9.5 mmol) of the (R)-(-)-methyl acetate prepared in Example D dissolved in 55 mL of dry toluene. The solution was cooled to -78° C. (CO2 /acetone) and 12 mL (12 mmol) of a 1.0M solution of DIBAL-H in toluene was added slowly (5 minutes) with stirring. The reaction mixture was stirred for 1 hour at -78° C. and poured into 100 g of ice and 100 mL of CHCl3. The reaction flask was rinsed with 100 mL of CHCl3 and the mixture was stirred vigorously for 30 minutes. After separation of the CHCl3 layer, the aqueous phase was washed with 100 mL of CHCl3 and the combined CHCl3 extracts were washed once with brine 80 mL, dried (Na2SO4) and concentrated leaving 2.5 g (93%) of the title aldehyde as a clear colorless oil of better than 95% purity (1H-NMR). The aldehyde was not further purified owing to its instability to temperatures above 60° C. and to silica gel: αD22 -33.71° (c=0.330, EtOH); 1H-NMR (CDCl3)δ9.47 (d, J=2.0 Hz, 1H), 7.33-7.32 (m, 4H), 4.95 (d, J=2.0 Hz, 1H), 0.92 (s, 9H), 0.10 (s, 3H), 0.02 (s, 3H).

1. customTo a 100 mL 2-necked round bottom flask equipped with a septurn and nitrogen inlet
2. additionwas added slowly (5 minutes)
3. stirringThe reaction mixture was stirred for 1 hour at -78° C.
4. washThe reaction flask was rinsed with 100 mL of CHCl3
5. stirringthe mixture was stirred vigorously for 30 minutes
6. customAfter separation of the CHCl3 layer
7. washthe aqueous phase was washed with 100 mL of CHCl3
8. washthe combined CHCl3 extracts were washed once with brine 80 mL
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated

ORD record

ord-af70fc9392ea4377ae2f1b8182edf4a7

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05399721