Triethylamine → HCID 57419667, compound

Temperature

0 °C

Crude diol from stage (i) (3.5 g, 18 mmol) was dissolved in DCM (60 mL) and treated with Et3N (10 mL, 72 mmol) and the solution was cooled to 0° C. Methanesulfonyl chloride (4.2 mL, 54 mmol) was added dropwise and the solution was stirred for 1 h being allowed to reach room temperature. The reaction was then quenched by the addition of water followed by 2M HCl (50 mL). The DCM layer was separated and the aqueous layer was re-extracted with DCM (50 mL). The combined organic fractions were washed with water (50 mL), dried (MgSO4) and concentrated to a volume of ca. 30 mL. Benzyltriethylammonium chloride (1 g) was added followed by a solution of sodium sulfide (5 g, 91 mmol) in water (50 mL). The mixture was stirred rapidly under a nitrogen atmosphere for 15 h. The organic layer was separated and the aqueous layer was re-extracted with DCM (50 mL). The combined organic layers were dried (MgSO4) and evaporated to a yellow oil. Flash chromatography afforded two fractions; the first was pure product and the second product contaminated with dimeric material. Trituration of the second fraction caused crystallisation of the dimeric material which was removed by filtration. The filtrate was combined with the first chromatography fraction to afford the desired product (800 mg, 23%); δH (CDCl3, 400 MHz) 4.16 (2H, s), 4.19 (2H, s), 4.48 (2H, m), 5.26 (1H, d), 5.37 (1H, d), 5.95-6.06 (1H, m), 6.74 (2H, m), 7.09 (1H, d).

1. customto reach room temperature
2. customThe reaction was then quenched by the addition of water
3. customThe DCM layer was separated
4. extractionthe aqueous layer was re-extracted with DCM (50 mL)
5. washThe combined organic fractions were washed with water (50 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated to a volume of ca. 30 mL
8. additionBenzyltriethylammonium chloride (1 g) was added
9. stirringThe mixture was stirred rapidly under a nitrogen atmosphere for 15 h
10. customThe organic layer was separated
11. extractionthe aqueous layer was re-extracted with DCM (50 mL)
12. dry with materialThe combined organic layers were dried (MgSO4)
13. customevaporated to a yellow oil
14. customFlash chromatography afforded two fractions
15. customcrystallisation of the dimeric material which
16. customwas removed by filtration

ORD record

ord-f88f5b29e2f34be6bff7756a2d5a649c

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610747B2