Dibromomethane → HCID 67160751, 화합물

HRID 2098430

반응식

HRID 2098430 반응식
C[Mg]Cl.O1CCCC1.[CH:9](=O)/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH3:17].BrCBr.C([Mg]Cl)(C)(C)C.C([O:30][CH2:31][CH3:32])C>>[CH:14](/[CH:15]1[CH2:17][CH:16]1[CH:31]([OH:30])[CH3:32])=[CH:13]\[CH2:12][CH2:11][CH2:10][CH3:9]

참가 물질

7

반응물 6

HCID 3024DibromomethaneHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 52833392,4-NonadienalHCID 178418310HCID 178418310, 화합물HCID 178418332HCID 178418332, 화합물

생성물 1

HCID 67160751HCID 67160751, 화합물수율 87.7%

실험 절차

Prepared as described in Example 1 (System B) from methyl magnesium chloride 3M in tetrahydrofuran (7.3 ml, 21 mmol), (2E,4E)-nona-2,4-dienal (3 g, 21 mmol), dibromomethane (15 g, 87 mmol) and tert-butyl magnesium chloride 2M in diethyl ether (43 ml, 87 mmol) at 0°-10° C. Work-up after 18 h and bulb-to-bulb distillation at 80° C./0.05 mbar gave 3.1 g (77%) of a colorless oil (syn/anti=83:17). Odour: fruity, pear, green. 1H NMR (CDCl3): δ 1H NMR (CDCl3): δ 0.5 (m, 1H), 0.7 (m, 1H), 0.8-1 (2H), 0.9 (t, 3H), 1.2-1.4 (6H), 1.8-2.0 (3H), 3.2 (m, 1H), 5.0 (m, 1H), 5.5 (m, 1H) ppm. 13C-NMR (CDCl3) syn-isomer: δ 11.5 (t), 13.9 (q), 18.8 (d), 22.2 (d), 22.5 (q), 28.1 (d), 31.7 (t), 32.1 (t), 71.5 (d), 128.9 (d), 131.7 (d). 13C-NMR (CDCl3) anti-isomer: δ 10.8 (t), 14.0 (q), 19.6 (d), 22.2 (d), 22.5 (q), 28.3 (d), 31.7 (t), 32.1 (t), 72.0 (d), 128.7 (d), 132.0 (d). syn-configuration assigned by GC retention time. MS (EI): m/z (%) 168 ([M]+, 1), 150 ([M-H2O]+, 7), 113 (48), 95 (47), 82 (33), 81 (80), 68 (72), 67 (100), 57 (43), 55 (45), 54 (80), 45 (75), 43 (56), 41 (64). IR (film): 3340 (br, OH), 2958 (m), 2925 (m), 2871 (m), 2858 (m), 1455 (m), 1414 (w), 1366 (m), 1290 (w), 1180 (w), 1103 (m), 1076 (m), 1029 (m), 959 (s), 897 (m).

후처리

  1. customPrepared
  2. distillationbulb-to-bulb distillation at 80° C./0.05 mbar

출처 및 근거

ORD 기록
ord-06711dd686524d78af01e4bf51005024
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450533B2

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