Hexane → HCID 18431832, compound

Temperature

-78 °C

In a round bottom flask equipped with a magnetic stirbar is placed 1,2-bis(trimethylsilyloxy)ethane (1.3 eq.) in CH2Cl2 containing trimethysilyltrifluoromethanesulfonate at -78° C. To this is added, within 20 minutes, a solution of 1 (1 eq) in CH2Cl2. The reaction is stirred for 1 hour at -78° C. and then slowly warmed to 25° C. for 1 hour. The reaction is quenched at 0° C. with water, extracted with CH2Cl2 (3 times), dried (MgSO4), and concentrated in vacuo to give crude 2. To a well stirred solution of crude 2 (1 eq) in methanol at 0° C. is added a suspension of sodium methoxide (1.2 eq) in MeOH. The reaction is stirred at 0° C. for 1 hour and then warmed to 25° C. for 1 hour. The reaction is neutralized with acidic ion exchange resin which is washed thoroughly with MeOH (5×). The filtrate is concentrated in vacuo to give a syrup which is subjected to flash chromatography on silica gel eluting with 4:1 hexane:ethyl acetate and 2% MeOH in CH2Cl2 to give 3.

1. customIn a round bottom flask equipped with a magnetic stirbar
2. additionTo this is added, within 20 minutes
3. temperatureslowly warmed to 25° C. for 1 hour
4. customThe reaction is quenched at 0° C. with water
5. extractionextracted with CH2Cl2 (3 times)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto give crude 2
9. stirringThe reaction is stirred at 0° C. for 1 hour
10. temperaturewarmed to 25° C. for 1 hour
11. washis washed thoroughly with MeOH (5×)
12. concentrationThe filtrate is concentrated in vacuo
13. customto give a syrup which

ORD record

ord-57b83a8c685d442f9f4280ebd7a8fbe5

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06048895