Chloromethyl Methyl Ether → HCID 66663661, compound

Participants

Reaction Conditions

Reaction Steps

To a round-bottom flask containing THF (80 ml) cooled to −78° C. and purged with a continuous stream of N2 gas was added KHMDS (1 M in THF, 22.6 ml, 4 eq.). In a separate flask purged with a continuous stream of N2 gas was added (R)-4-benzyl-3-(6-bromohexanoyl)oxazolidin-2-one (2.00 g, 1 eq.) dissolved in THF (10 ml) and cooled to −78° C. The solution containing (R)-4-benzyl-3-(6-bromohexanoyl)oxazolidin-2-one was transferred to the KHMDS solution, and chloro(methoxy)methane (7.2 g, 15.8 eq.) was added dropwise. The reaction mixture was allowed to stir for an additional 2 h, quenched with saturated aqueous NH4Cl and concentrated. Water was added. The mixture was extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. Silica gel chromatography using 30-100% DCM-heptane yields the title compound.

Provenance & Evidence