4-Methoxybenzaldehyde → HCID 66930896, compound

To a suspension of 6-phenoxyhexyltriphenylphosphonium bromide (6.1) (4.60 g, 8.86 mmol) in dry THF (80 mL) at 0° C., under an argon atmosphere was added potassium bis(trimethylsilyl)amide (1.76 g, 8.86 mmol). The resulting slurry was stirred for 5 min at the same temperature and then a solution of 4-methoxybenzaldehyde (0.61 g, 4.46 mmol) in dry THF (10 mL) was added. The reaction mixture was stirred for an additional 10 min and quenched with saturated aqueous NH4Cl (20 mL). The resulting mixture was warmed to room temperature, diluted with Et2O (100 mL), the organic phase was separated and the aqueous phase extracted with Et2O. The combined organic layer was washed with brine, dried over MgSO4 and the solvent evaporated under reduced pressure. The residue obtained was purified through a short column of silica gel, eluting with 5% Et2O-hexane, to give the product 7.1 (1.21 g, 92% yield, predominantly cis, cis:trans=96:4) as a colorless liquid.

1. stirringThe reaction mixture was stirred for an additional 10 min
2. customquenched with saturated aqueous NH4Cl (20 mL)
3. additiondiluted with Et2O (100 mL)
4. customthe organic phase was separated
5. extractionthe aqueous phase extracted with Et2O
6. washThe combined organic layer was washed with brine
7. dry with materialdried over MgSO4
8. customthe solvent evaporated under reduced pressure
9. customThe residue obtained
10. customwas purified through a short column of silica gel
11. washeluting with 5% Et2O-hexane

ORD record

ord-ebfd06cc388c440a8eb021f4c2ed2fc6

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102622B2