Water → HCID 18784902, compound

To a stirred solution of methyl 2,2-diethyl-4-pentenoate (Canney D J, Holland K D, Levine J A, McKeon A C, Ferrendelli J A, Covey D F (1991), supra.)(5.10 g, 30 mmol) in dry THF (10 mL), was added BH3.THF (1M, 12 mL, 12 mmol) slowly over a period of 15 min at 0° C. in a nitrogen atmosphere. After 2 h at 0° C., the reaction mixture was allowed to warm to room temperature (ca. 2 h). The reaction flask was immersed in an ice bath; water (5 mL) was added to destroy residual hydride, and the reaction mixture was oxidized by adding NaOH (3N, 3.2 mL) and then slowly adding 30% hydrogen peroxide (3.2 mL). After stirring for 1.5 h, the solution was poured into water (100 mL), and extracted with ether (3×50 mL). The combined ether extract was washed with 50 mL portions of water and brine, dried over MgSO4, and the solvent removed in vacuo to give 6.04 g of colorless oil. Column chromatography over silica gel (gradient elution, hexanes-EtOAc, 4:1 to 1:1) afforded the pure hydroxyester (2.79 g, 50%) as a colorless liquid.

1. customThe reaction flask was immersed in an ice bath
2. customto destroy residual hydride
3. additionby adding NaOH (3N, 3.2 mL)
4. additionslowly adding 30% hydrogen peroxide (3.2 mL)
5. additionthe solution was poured into water (100 mL)
6. extractionextracted with ether (3×50 mL)
7. extractionThe combined ether extract
8. washwas washed with 50 mL portions of water and brine
9. dry with materialdried over MgSO4
10. customthe solvent removed in vacuo

ORD record

ord-b6106cfdb56942228fad6c721a7c5b9d

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05776959