8,8-Dibutyl-7,9-dioxa-8-stannaspiro[4.5]dec-2-ene → 11,11-Diethyl-7,9,13,14-tetraoxadispiro[4.2.5.2]pentadec-1-ene

HRID 990158노트

반응식

HRID 990158 반응식
C([Sn]1(CCCC)[O:14][CH2:13][C:8]2([CH2:12][CH:11]=[CH:10][CH2:9]2)[CH2:7][O:6]1)CCC.[CH2:19]([C:21]1([CH2:28][CH3:29])[CH2:26][O:25][C:24](=S)[O:23][CH2:22]1)[CH3:20]>>[CH2:19]([C:21]1([CH2:28][CH3:29])[CH2:26][O:25][C:24]2([O:6][CH2:7][C:8]3([CH:9]=[CH:10][CH2:11][CH2:12]3)[CH2:13][O:14]2)[O:23][CH2:22]1)[CH3:20]

참가 물질

3

반응물 2

HCID 187669458,8-Dibutyl-7,9-dioxa-8-stannaspiro[4.5]dec-2-eneHCID 187669565,5-Diethyl-1,3-dioxane-2-thione

생성물 1

HCID 1876694411,11-Diethyl-7,9,13,14-tetraoxadispiro[4.2.5.2]pentadec-1-ene수율 72%

실험 절차

To the above solution of 8,8-dibutyl-7,9-dioxa-8-stannaspiro[4.5]dec-2-ene 4 was added 5,5-diethyl-1,3-dioxane-2-thione 1 (10.1 g, 60.3 mmol) in several small portions at room temperature over a period of 20 min. The resulting mixture was allowed to stir at room temperature for 24 hours. The reaction was monitored by TLC (silica gel, 25% ether/hexanes). The reaction mixture was then concentrated under reduced pressure and the residue taken up with ethyl ether (white suspension formed upon standing). The ether solution was filtered and concentrated under reduced pressure to give light yellowish oil. The crude material was purified by column chromatography (silica gel, 10-15% ethyl ether/hexanes). The desired 11,11-diethyl-7,9,13,14-tetraoxadispiro[4.2.5.2]pentadec-1-ene (DECP 5) was obtained as white solid in 72% yield. Mp (DSC) 95.19° C., 1H-NMR (CD13, 300 MHz) δ5.60 (s, 2H), 3.80 (s, 4H), 3.69 (s, 4H), 2.27 (s, 4H), 1.45-1.37 (q, 4H, J-7.8 Hz), 0.82-0.77 (t, 6H, J=7.8 Hz); 13C-NMR (CD13, 300 MHz) δ128.52, 114.39, 71.04, 69.48, 39.76, 34.33, 23.16, 7.12; FT-IR (Kbr pellet) (cm1) 3053, 2968, 1619, 1457, 1360, 1266, 1212, 1178, 1001, 938; Anal. Calcd for C1H2404: C, 67.14; H, 901; Found: C, 67.44; H, 9.22.

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. filtrationThe ether solution was filtered
  3. concentrationconcentrated under reduced pressure
  4. customto give light yellowish oil
  5. customThe crude material was purified by column chromatography (silica gel, 10-15% ethyl ether/hexanes)

출처 및 근거

ORD 기록
ord-22c1ee0d690b4821a28eb19d72da78df
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458865B2

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