Triethylamine → HCID 86685133, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.76 mL, 8.91 mmol) was dissolved in 10 mL methylene chloride and cooled to −78° C., followed by dropwise addition of 10 mL of mixed solution (methylene chloride and dimethyl sulfoxide, v:v=10:0.85). The reaction mixture was stirred for 15 minutes. Then 25 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 5h (4.2 g, 5.94 mmol) in methylene chloride was dropwise added before the mixture was stirred for 40 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours after triethylamine (4.29 mL, 29.69 mmol) was dropwise added. Thereafter, the reaction mixture was partitioned after 35 mL 1 M hydrochloric acid were added, the organic extract was washed with saturated sodium chloride solution (35 mL×2), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmeth-yl)phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 51 (4.19 g, pale yellow grease), which was used directly in the next step without purification.

Provenance & Evidence