Dibromomethane → HCID 67159715, compound

HRID 2098432Notes

Reaction equation

HRID 2098432 reaction equation
[CH2:1]([C:3]1[CH2:7][CH2:6][C:5](=O)[C:4]=1[CH3:9])[CH3:2].C[Li].C([O:14][CH2:15][CH3:16])C.BrCBr.C([Mg]Cl)(C)(C)C>O>[CH2:7]([C@:3]12[CH2:9][C@@:4]1([CH3:5])[C:15]([CH3:16])([OH:14])[CH2:2][CH2:1]2)[CH3:6]

Participants

7

Reactant 5

HCID 3024DibromomethaneHCID 3283Diethyl Ether2×HCID 13119715HCID 13119715, compoundHCID 178418310HCID 178418310, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 67159715HCID 67159715, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared as described in Example 20 (System B) from 3-ethyl-2-methylcyclopent-2-enone (4 g, 32 mmol) (G. Berube, A. G. Fallix, Can. J. Chem. 69, 77-78, 1991), addition of methyl-lithium 1.6 M in diethyl ether (28 ml, 45 mmol) at −20° C., dibromomethane (2×8.4 g, 97 mmol) and tert-butyl magnesium chloride 2M in diethyl ether (2×24 ml, 97 mmol). Work-up after 18 h at 25° C. (as described in example 1) and bulb-to-bulb distillation gives 3 g (60%) of a waxy yellowish solid. 1H NMR (CDCl3): δ-0.1 (d, 1H), 0.75 (d, 1H), 0.95 (t, 3H), 1.1 (s, 3H), 1.25 (s, 1H), 1.2-1.3 (1H), 1.3-1.4 (2H), 1.5-1.6 (2H), 1.7 (1H) ppm. 13C-NMR (CDCl3): δ 11.4 (q), 12.7 (q), 18.4 (t), 24.9 (q), 25.8 (t), 28.5 (t), 32.35 (s), 34.6 (s), 36.5 (t), 81.3 (s). Cis-configuration determined by NMR-analysis in water-free DMSO. MS (EI): m/z (%) 154 (M+, 1), 139 ([M-15]+, 38), 136 ([M-18]+, 67), 125 (37), 121 (27), 107 (86), 96 (59), 81 (100), 67 (30), 57 (42), 55 (36), 43 (86), 41 (40). IR (film): 3297 (br, OH), 2959 (s), 2859 (m), 1452 (s), 1365 (s), 1300 (m), 1199 (s), 1167 (m), 1115 (vs), 1062 (m), 970 (s), 938 (s), 926 (s).

Workup

  1. customPrepared
  2. distillation(as described in example 1) and bulb-to-bulb distillation
  3. customgives 3 g (60%) of a waxy yellowish solid

Sources & evidence

ORD record
ord-4c96ebcef25f4694b581f971aff51177
Source dataset
uspto-grants-2013_05
Patent number
US08450533B2

Reaction notes

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