1,2-Dimethoxyethane → methyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate

0.5M Potassium bis(trimethylsilyl)amide toluene solution (8.48 ml, 4.24 mmol) was added dropwise to a DME (40 ml) solution of methyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)sulfonyl]pent-2-enoate (1.19 g, 3.53 mmol) at −60° C. and the reaction solution was stirred at the same temperature for 30 minutes. Subsequently a THF (5 ml) solution of (2R,3S)-2-methyl-3-[(triethylsilyl)oxy]pentanal (1.63 g, 7.06 mmol) was added dropwise at −78° C. and the reaction solution was stirred for two hours. After the reaction solution was warmed to room temperature, distilled water was added. The reaction solution was diluted with ethyl acetate and washed with brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=50:1) to obtain the title compound (1.17 g) as a colorless oil. The title compound was determined to be a mixture of E:Z 17:1 by 1H-NMR.

1. stirringthe reaction solution was stirred for two hours
2. distillationdistilled water
3. additionwas added
4. additionThe reaction solution was diluted with ethyl acetate
5. washwashed with brine
6. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
7. filtrationthe drying agent was filtered off
8. concentrationthe organic layer was concentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=50:1)

ORD record

ord-2ecb9eaa840b40afa69831950a1630bb

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816401B2