Dibromomethane → HCID 67160832, compound

HRID 2098433

Reaction equation

HRID 2098433 reaction equation
C[Li].[C:3](OC)(=O)/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].BrCBr.[C:18]([Mg]Cl)(C)(C)C.C([O:26][CH2:27][CH3:28])C>>[CH2:8]([C@@H:9]1[CH2:11][C@H:10]1[C:27]([OH:26])([CH3:28])[CH3:18])[CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Participants

6

Reactant 5

HCID 3024DibromomethaneHCID 3283Diethyl Ether3×HCID 5368076Methyl 2-nonenoateHCID 178418310HCID 178418310, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 67160832HCID 67160832, compoundYield 74%

Procedure

Prepared as described in Example 23 from methyl lithium 1.6 M in diethyl ether (7.4 ml, 12 mmol) and (E)-methyl non-2-enoate (Neofolione) (1 g, 6 mmol) in diethyl ether (10 ml) at −78° C., followed by dibromomethane (5×1 g, 30 mmol) and tert-butyl magnesium chloride 2M in diethyl ether (5×3 ml, 30 mmol) at 0°-5° C. Work-up after 18 h at 25° C. and bulb-to-bulb distillation under high vacuum gives 0.8 g (74%) of a colorless oil. 1H NMR (CDCl3): δ 0.15 (m, 1H), 0.45 (m, 1H), 0.7 (2 m, 2H), 1.15 (s, 3H), 1.2 (s, 3H), 1.2-1.4 (7H) ppm. 13C-NMR (CDCl3): δ 8.1 (t), 14.1 (q), 15.1 (d), 22.6 (t), 28.4 (q), 28.9 (q), 29.2 (t), 29.4 (t), 30.3 (d), 31.9 (t), 34.1 (t), 69.7 (s). MS (EI): m/z (%) 169 ([M-15]+, 19), 151 (3), 123 (4), 110 (11), 109 (12), 97 (14), 95 (37), 72 (88), 71 (89), 43 (100). IR (film): 3377 (br, OH), 2960 (m), 2922 (s), 2853 (m), 1464 (m), 1367 (m), 1229 (w), 1145 (m), 944 (m), 915 (m).

Workup

  1. customPrepared
  2. distillationbulb-to-bulb distillation under high vacuum

Sources & evidence

ORD record
ord-704a8555a31b44238e9af5a8ad10f36b
Source dataset
uspto-grants-2013_05
Patent number
US08450533B2

Linked notes

Loading…