1,2-Dibromoethane → HCID 19885932, compound

HRID 654947Notes

Reaction equation

HRID 654947 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Mg]Br.BrCCCCCCCCC1SC=CC=1.[Mg].BrCCBr.[CH3:35][Si:36]([CH3:45])([CH3:44])[C:37]1[O:41][CH:40]=[C:39]([CH:42]=[O:43])[CH:38]=1>O1CCCC1>[OH:43][CH:42]([C:39]1[CH:38]=[C:37]([Si:36]([CH3:45])([CH3:44])[CH3:35])[O:41][CH:40]=1)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 21705970HCID 21705970, compoundHCID 178419678HCID 178419678, compound

Product 1

HCID 19885932HCID 19885932, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 8-(thiophene-2-yl)octyl magnesium bromide [0.62 mmol, prepared from 1-bromo-8-(thiophen-2-yl)octane; 0.170 g, 0.620 mmol and 1.24 mmol magnesium with a catalytic amount of 1,2 dibromoethane as initiator] in tetrahydrofuran (2 ml) at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.104 g, 0.620 mmol) in tetrahydrofuran (3 ml). The solution was warmed to room temperature, stirred for one hour, quenched with saturated ammonium chloride solution and extracted into ethyl ether. The organic portion was washed with saturated sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to a yellow oil. Purification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane) gave the desired alcohol.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. extractionextracted into ethyl ether
  3. washThe organic portion was washed with saturated sodium bicarbonate solution, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. customPurification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-52607143f4244f858675f778ce1534f5
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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