Ammonium Chloride → HCID 18510261, Verbindung

To a solution of the TMS cyanohydrin from Example 1, Step 1 (3.70 g, 16.6 mmol) in THF (40 mL) under N2 at −78° C. was added slowly a solution of LHMDS (18.2 mL, 18.2 mmol, 1.0 M/THF). After 15 min. at −78° C., a solution of methyl 3-(bromomethyl)benzoate (3.99 g, 17.4 mmol) in THF (20 mL) was added via double-tipped needle. The reaction was allowed to warm slowly to r.t. over 1 h. and was then stirred at r.t. for 2.5 h. Bu4NF (33 mL, 33 mmol, 1M/THF) was then added and the mixture was stirred for 1 h. Saturated NH4Cl (20 mL) was then added and the product was extracted with EtOAc. The organic phase was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. The residue was stirred vigourously with 1:5 Et2O:hexane (50 mL) for 1 h, and the product was then obtained by filtration. This material was dissolved in CH2Cl2 and filtered through a plug of silica gel, washing with CH2Cl2. After removal of solvent, a pale yellow solid (3.4 g) was obtained.

1. stirringthe mixture was stirred for 1 h
2. extractionthe product was extracted with EtOAc
3. washThe organic phase was washed with H2O and brine
4. dry with materialwas then dried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. stirringThe residue was stirred vigourously with 1:5 Et2O
8. waithexane (50 mL) for 1 h
9. customthe product was then obtained by filtration
10. filtrationfiltered through a plug of silica gel
11. washwashing with CH2Cl2
12. customAfter removal of solvent

ORD-Eintrag

ord-94b4f214fba0441783c74c7372d4f92c

Quelldatensatz

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06583126B2