1,2-Dibromoethane → HCID 54310569, compound

HRID 654949Notes

Reaction equation

HRID 654949 reaction equation
[O:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Mg]Br)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].BrCCCCCCCCO[Si](C(C)(C)C)(C)C.[Mg].BrCCBr.[CH3:41][Si:42]([CH3:51])([CH3:50])[C:43]1[O:47][CH:46]=[C:45]([CH:48]=[O:49])[CH:44]=1>O1CCCC1>[OH:49][CH:48]([C:45]1[CH:44]=[C:43]([Si:42]([CH3:51])([CH3:50])[CH3:41])[O:47][CH:46]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 10969362Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178455211HCID 178455211, compound

Product 1

HCID 54310569HCID 54310569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 8-t-butyldimethylsiloxyoctylmagnesium bromide (5.63 mmol prepared from 1-bromo-8-t-butyldimethylsiloxyoctane 1.82 g, 5.63 mmol and 6.19 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 (0.866 g, 5.15 mmol) in tetrahydrofuran (10 ml). The solution was warmed to room temperature, stirred for one hour, quenched with cold 10% hydrochloric acid and extracted into ethyl ether. The organic portion was washed with saturated sodium bicarbonate, water saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a pale oil. Purification by flash chromatography (silica, 5 to 10% ethyl acetate/hexane) gave the desired alcohol.

Workup

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

Sources & evidence

ORD record
ord-7886fa1c1d4a47ed87b017fd930a3747
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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