1,2-Dibromoethane → HCID 19885911, compound

HRID 654900Notes

Reaction equation

HRID 654900 reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Mg]Br)=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2.S1C(CCCCCCBr)=CC2C=CC=CC1=2.[Mg].BrCCBr.[CH3:39][Si:40]([CH3:49])([CH3:48])[C:41]1[O:45][CH:44]=[C:43]([CH:46]=[O:47])[CH:42]=1>O1CCCC1>[S:1]1[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:46]([C:43]2[CH:42]=[C:41]([Si:40]([CH3:49])([CH3:48])[CH3:39])[O:45][CH:44]=2)[OH:47])=[CH:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 19785619HCID 19785619, compoundHCID 178419676HCID 178419676, compound

Product 1

HCID 19885911HCID 19885911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 6-(benzo[b]thien-2-yl)hexylmagnesium bromide (1.22 mmol, prepared from 1.22 mmol 6-(benzo[b]thien-2-yl)-1-bromohexane and 2.44 mmol magnesium, initiated with a catalytic amount of 1,2-dibromoethane) in 1.5 ml tetrahydrofuran at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.167 g., 0.99 mmol) in 1 ml tetrahydrofuran. This solution was allowed to warm to room temperature, stirred for 30 minutes, and then quenched with a 5% ammonium chloride solution. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give a pale yellow oil. This material was purified by flash chromatography (silica, 100% hexane to 20% ethyl acetate/hexane) to give the desired alcohol.

Workup

  1. customat 0°
  2. customquenched with a 5% ammonium chloride solution
  3. customThe resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
  4. washThe organic portion was washed with water, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a pale yellow oil
  9. customThis material was purified by flash chromatography (silica, 100% hexane to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7a7ea8d504764d24930b2d59227628e3
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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