反应详情

Borane-dimethylsulfide complex (3.5 mL of 2 M in ether, 7 mmol) was added dropwise to a cooled (5° C.) solution of 4-{1-[4-(tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (see step (i) above; 4.6 g, 13 mmol) in dry THF over a period of 15 min. The resulting mixture was stirred at between 0 and 5° C. for 1.5 h. Stirring was then continued for a further 4 h at rt. Water (14 mL) and NaBO3 (5 g) were added and the mixture stirred overnight. Ether was added and the resulting organic layer was separated, washed with water and brine, dried and then evaporated. The resulting residue was purified by chromatography on silica gel, eluting with IPA:EtOAc:heptane (5:20:70), to give 2.44 g (58%) of the sub-title compound.

1. stirringStirring
2. waitwas then continued for a further 4 h at rt
3. stirringthe mixture stirred overnight
4. customthe resulting organic layer was separated
5. washwashed with water and brine
6. customdried
7. customevaporated
8. customThe resulting residue was purified by chromatography on silica gel
9. washeluting with IPA:EtOAc:heptane (5:20:70)