Acetaldehyde → HCID 86706087, 화합물

A solution of N,N-diisopropylamine (909 mg, 1.25 mL, 9 mmol) in tetrahydrofuran (4 mL) was stirred at −78° C. under nitrogen. n-Butyllithium (3.6 mL, 9 mmol, 2.5 M solution in hexane) was added dropwise and the reaction mixture was stirred at −78° C. for 30 minutes. A solution of tetrahydro-pyran-2-carboxylic acid methyl ester (864 mg, 6 mmol) in tetrahydrofuran (8 mL) was added and the reaction mixture was stirred at −78° C. for 20 minutes. Acetaldehyde (792 mg, 1.0 mL, 18 mmol) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was cooled to 0° C. and ice-cold hydrochloric acid (2 M) was added to acidify the reaction mixture to pH 2. Sodium chloride was added to saturate the aqueous phase and the mixture was extracted with diethyl ether. The organic extracts were combined and washed with brine. The organic solution was filtered through a hydrophobic frit and the filtrate was evaporated. The residue was purified by silica gel chromatography using a gradient of pentane/diethyl ether 1:1 to 0:1 to afford the title compound (1.28 g) as an oil and as a 2:1 mixture of diastereoisomers. LCMS (m/z) 189.3 [M+H], Tr=1.23 min.

1. stirringthe reaction mixture was stirred at −78° C. for 20 minutes
2. customThe cooling bath was removed
3. stirringthe reaction mixture was stirred at room temperature for 1 h
4. temperatureThe reaction mixture was cooled to 0° C.
5. additionice-cold hydrochloric acid (2 M) was added
6. additionSodium chloride was added
7. concentrationto saturate the aqueous phase
8. extractionthe mixture was extracted with diethyl ether
9. washwashed with brine
10. filtrationThe organic solution was filtered through a hydrophobic frit
11. customthe filtrate was evaporated
12. customThe residue was purified by silica gel chromatography

ORD 기록

ord-42b508da4dcb4c8d984d6ea645bdecc7

출처 데이터셋

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09062092B2