Undecanal → Tridec-1-en-3-ol

HRID 1458302

반응식

HRID 1458302 반응식
[CH:1]([Mg]Br)=[CH2:2].[CH:5](=[O:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>[Cl-].[NH4+]>[CH2:1]=[CH:2][CH:5]([OH:16])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

참가 물질

4

반응물 2

HCID 8186UndecanalHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 185797Tridec-1-en-3-ol

시약·촉매·용매 1

HCID 25517Ammonium Chloride용매

실험 절차

To a solution of vinyl magnesium bromide in tetrahydrofuiran (1M, 82.0 mL) at 0° C. was added a solution of undecanal i (7.00 g, 41.1 mmol) in tetrahydrofuiran (25 mnL) in about 10 min. After 6 h at 0° C., saturated ammonium chloride solution (50 mL) was added. The two layers were separated. The water layer was extracted with ether (2×50 mL). The combined organic solutions were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexane) to give 7.94 g (98%) of i-a as a colorless oil: IR (neat) 3409, 3079, 1644, and 1463 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 5.80 (ddd, 1 H, J=6.3, 10.7, and 17.2 Hz, CH=CH2), 5.55 (dd, 1 H, J=17.2 and 1.4 Hz, CH=CH2), 5.05 (dd, 1 H, J=10.7 and 1.4 Hz, CH=CH2), 3.99 (q, 1 H, J=6.2 Hz, CHOH), 2.58 (br s, 1 H, OH, 1.46-1.22 [m, 18 H, C(4-12)H2 ], and 0.83 (t, J=6.4 Hz, CH2CH3); 13C NMR (CDCl3, 75.5 MHz) δ 141.61, 114.50, 73.33, 37.24, 32.12, 29.83, 29.55, 25.57, 22.87, and 14.26.

후처리

  1. customThe two layers were separated
  2. extractionThe water layer was extracted with ether (2×50 mL)
  3. dry with materialThe combined organic solutions were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10% ethyl acetate in hexane)
  7. customto give 7.94 g (98%) of i-a as a colorless oil

출처 및 근거

ORD 기록
ord-725e5a1b83d94a588a6ed606525226a5
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849936

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