Dibromomethane → (RS)-1-((1RS,2SR)-2-((E)-hex-1-enyl)cyclopropyl)ethanol

HRID 2098430

Reaktionsgleichung

Reaktionsgleichung von HRID 2098430
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]

Komponenten

7

Edukt 6

HCID 3024DibromomethaneHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 52833392,4-NonadienalHCID 178418310HCID 178418310, VerbindungHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 67160751(RS)-1-((1RS,2SR)-2-((E)-hex-1-enyl)cyclopropyl)ethanolAusbeute 87,7 %

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-06711dd686524d78af01e4bf51005024
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450533B2

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