Реакция #2200582

Уравнение реакции

water

(2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol

Et3N

ether

→

(2S,3S)-2-methyl-3-tetrahydropyranyloxybutyraldehyde

Выход 101.0%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   workup.WAITat room temperature for 1 hour
2. 2
   ЭкстракцияThe aqueous layer was extracted with ether
3. 3
   ПромывкаThe combined ether extracts were washed with 1M HCl, water, saturated NaHCO3, brine, and they
4. 4
   Сушкаwere dried over Na2SO4
5. 5
   Другоеevaporated in order

Методика

The Py.SO3 complex (7.06 g, 44.36 mmol) was added in portions at 0° C. to a solution of (2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol (5) (1.39 g, 7.39 mmol) and anhydrous Et3N (4.94 g, 6.78 ml, 48.77 mmol) in DMSO (25 ml). The reaction mixture was stirred at 0° C. for 3 hours, and then at room temperature for 1 hour, and then it was divided between water and ether. The aqueous layer was extracted with ether. The combined ether extracts were washed with 1M HCl, water, saturated NaHCO3, brine, and they were dried over Na2SO4 and evaporated in order to obtain crude (2S,3S)-2-methyl-3-tetrahydropyranyloxybutyraldehyde (6) (1.39 g, 100%) which was used directly for the next reaction without purification: 1H NMR (250 MHz, CDCl3) δ 9.78 (d, J=2.7 Hz, 0.5H); 9.74 (d, J=2.0 Hz, 0.5H); 4.76 to 4.62 (m, 1H); 4.15 to 3.73 (m, 2H); 3.53 to 3.43 (m, 1H); 2.62 to 2.46 (m, 1H); 1.82 to 1.51 (m, 6H); 1.29 (d, J=6.2 Hz, 1.5H); 1.18 (d, J=6.2 Hz, 1.5H); 1.11 (d, J=7.2 Hz, 1.5H); 1.07 (d, J=7.1 Hz, 1.5H); 13C NMR (62.5 MHz, CDCl3) δ 203.5; 203.1; 99.0; 95.1; 74.4; 71.0; 62.0; 51.6; 51.1; 30.5; 25.0; 19.2; 19.1; 18.6; 16.0; 9.7; 9.1; MS (CI) m/z 187. [M+H]+.

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