Hydrochloric Acid → HCID 86594399, compound

Temperature

-78 °C

An oven-dried 1Lthree-neck round bottom flask equipped with a magnetic stir bar and a −100° C. thermometer was charged with 206 mL of anhydrous THF and KOtBu (28.2 g, 250 mmol). This mixture was flushed with Ar and cooled to −78° C., then cis-2-butene (23 mL, 250 mmol), condensed from a gas lecture bottle into a rubber-stoppered round bottom flask immersed in a −78° C. dry ice-acetone bath, was poured into the reaction mixture. n-BuLi (100 mL, 2.5 M in hexane) was then added dropwise via cannula over 1.5 h. After completion of the addition, the cooling bath was removed and the reaction mixture was allowed to warm to −20 to −25° C. for 30 min before being recooled to −78° C. Triisopropylborate (57.8 mL, 250 mmol) was added drop-wise via cannula to the (Z)-crotylpotassium solution over 2 h. After addition, the reaction mixture was maintained at −78° C. for 30 min and then rapidly poured into a 2L separatory funnel containing 470 mL of 1 N HCl saturated with NaCl. The aqueous layer was adjusted to pH 1 by using 1 N HCl (100-150 mL), and then a solution of (R,R) -diisopropyl tartrate (52.8 g, 250 mmol) in 88 mL of Et2O was added. The phases were separated, and the aqueous layer was extracted with additional Et2O (4×120 mL). The combined extracts were dried over MgSO4 for 1 h then vacuum filtered through a fritted glass funnel under Ar blanket into an oven-dried round-bottom flask. The filtrate was concentrated in vacuo, and pumped to constant weight at under vacuum. Anhydrous toluene (170 mL) was added to the flask make a 1M solution.

1. customAn oven-dried 1Lthree-neck round bottom flask equipped with a magnetic stir bar and a −100° C.
2. customThis mixture was flushed with Ar
3. customimmersed in a −78° C.
4. additionwas poured into the reaction mixture
5. additionAfter completion of the addition
6. customthe cooling bath was removed
7. temperatureto warm to −20 to −25° C. for 30 min
8. custombefore being recooled to −78° C
9. additionAfter addition
10. temperaturethe reaction mixture was maintained at −78° C. for 30 min
11. customThe phases were separated
12. extractionthe aqueous layer was extracted with additional Et2O (4×120 mL)
13. dry with materialThe combined extracts were dried over MgSO4 for 1 h
14. filtrationvacuum filtered through a fritted glass funnel under Ar blanket into an oven-dried round-bottom flask
15. concentrationThe filtrate was concentrated in vacuo
16. additionAnhydrous toluene (170 mL) was added to the flask

ORD record

ord-b216c0bb6b1048faa30bb9726ad48a74

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968736B2