Ethyl 2-formylcyclopropanecarboxylate → Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

To a solution of ethyl 2-formylcyclopropanecarboxylate (2.00 g, 13.68 mmol) in absolute ethanol (55.0 mL) at room temperature and under an anhydrous atmosphere was added sodium borohydride (0.776 g, 20.53 mmol) in one portion. The reaction mixture was stirred at room temperature for 5 h then quenched with an aqueous pH 7 phosphate buffer solution (100 mL) and the ethanol was removed under reduced pressure. The aqueous layer was mixed with methylene chloride (100 mL), decanted, then extracted with methylene chloride (2×100 mL). The combined organic extracts were then successively washed with an aqueous pH 7 phosphate buffer solution (70 mL) and brine (70 mL), dried over MgSO4, filtered, and concentrated to give ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (C-5) as a light yellow oil (1.334 g, 68% yield), which was used for the next step without additional purification. MS (M+1): m/e 145.

1. customthen quenched with an aqueous pH 7 phosphate buffer solution (100 mL)
2. customthe ethanol was removed under reduced pressure
3. additionThe aqueous layer was mixed with methylene chloride (100 mL)
4. customdecanted
5. extractionextracted with methylene chloride (2×100 mL)
6. washThe combined organic extracts were then successively washed with an aqueous pH 7 phosphate buffer solution (70 mL) and brine (70 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-d062a491fd814eda9ed076f0ae077e43

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716312B2