Undecanal → Tridec-1-en-3-ol

HRID 1081972

반응식

HRID 1081972 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+]>O1CCCC1>[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

5

반응물 3

HCID 8186UndecanalHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 185797Tridec-1-en-3-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of vinyl magnesium bromide in tetrahydrofuran (1M, 82.0 mL) at 0° C. was added a solution of undecanal i (7.00 g, 41.1 mmol) in tetrahydrofuran (25 mL) 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) δ5.80 (ddd, 1H, J=6.3, 10.7, and 17.2 Hz, CH=CH2), 5.55 (dd, 1H, J=17.2 and 1.4 Hz, CH=CH2), 5.05 (dd, 1H, J=10.7 and 1.4 Hz, CH=CH2), 3.99 (q, 1H, J=6.2 Hz, CHOH), 2.58 (br s, 1H, OH), 1.46-1.22 [m, 18H, C(4-12)H2 ], and 0.83 (t, J=6.4 Hz, CH2CH3); 13C NMR (CDCl3, 75.5 MHz) δ141.61, 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-8abb01bcb7484fa9a5d660778ad70dcf
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587491

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