Ethyl Propionate → HCID 22184688, 화합물

HRID 968192노트

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HRID 968192 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([CH:15]([CH2:19][CH3:20])[CH2:16][C:17]#[N:18])[CH3:14].[C:21](OCC)(=[O:24])[CH2:22][CH3:23]>C1COCC1.CCCCCC>[C:17]([CH:16]([CH:15]([CH2:19][CH3:20])[CH2:13][CH3:14])[C:21](=[O:24])[CH2:22][CH3:23])#[N:18]

참가 물질

7

반응물 4

HCID 7749Ethyl PropionateHCID 7912DiisopropylamineHCID 128361403-EthylpentanenitrileHCID 178418339Butyllithium

생성물 1

HCID 22184688HCID 22184688, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

Part B. A solution of diisopropylamine (7.50 mL, 57.2 mmol) in THF (100 mL) was cooled to −78° C., and treated with n-butyllithium (34.0 mL of a 1.6 M solution in hexane). The solution was warmed briefly to 0° C., and then recooled to −78° C. The nitrile compound from Part A was then added by syringe, and the solution was allowed to stir for 1 hour. Then, ethyl propionate (6.50 mL, 56.7 mmol) was added by syringe, and the resulting mixture was allowed to stir and warm to ambient temperature for 12 hours. It was poured into 200 mL of satd. aq. NH4Cl solution, and this was extracted with ethyl acetate (2×200 mL). The extracts were combined, dried over magnesium sulfate, filtered and evaporated. The residual oil was separated by column chromatography (silica gel, 10:90 ethyl acetate-hexane) to afford the product, 4-cyano-5-ethyl-3-heptanone, as an oil 4.06 g, 24.3 mmol, 49%). TLC RF 0.47 (20:80 ethyl acetate-hexane). Spectral data: 1H NMR (300 MHz, CDCl3): δ 3.49 (1H, d, J=4.4 Hz), 2.74 (2H, q, J=7.3 Hz), 2.08-1.98 (1H, m), 1.70-1.58 (1H, m), 1.50-1.20 (3H, m), 1.12 (3H, t, J=7.3 Hz), 0.95 (3H, t, J=7.3 Hz), 0.91 (3H, t, J=7.3 Hz). MS (H2O-GC/MS): m/e 167 (100).

후처리

  1. customrecooled to −78° C
  2. stirringto stir
  3. temperaturewarm to ambient temperature for 12 hours
  4. additionIt was poured into 200 mL of satd
  5. extractionaq. NH4Cl solution, and this was extracted with ethyl acetate (2×200 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residual oil was separated by column chromatography (silica gel, 10:90 ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-dfa59a98db9a46b681b8c4b22c728857
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958341B2

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