Sulfuric Acid → HCID 19885953, compound

HRID 654893Notes

Reaction equation

HRID 654893 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCCCC1C=CC=CC=1.[Mg].[CH3:23][Si:24]([CH3:33])([CH3:32])[C:25]1[O:29][CH:28]=[C:27]([CH:30]=[O:31])[CH:26]=1.S(=O)(=O)(O)O>C(OCC)C>[OH:31][CH:30]([C:27]1[CH:26]=[C:25]([Si:24]([CH3:33])([CH3:32])[CH3:23])[O:29][CH:28]=1)[CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 12503(3-Bromopropyl)benzeneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 19885953HCID 19885953, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3-phenylpropylmagnesium bromide (3.3 ml of an 0.313M solution in ethyl ether, 1.03 mmol, generated from 1-bromo-3-phenylpropane and magnesium) at 0° under argon, was added dropwise 5-trimethylsilyl-3-furaldehyde (0.145 g., 0.862 mmol) in 5 ml ethyl ether. This solution was allowed to warm to room temperature, stirred for one hour, and then poured over crushed ice containing several drops of concentrated sulfuric acid. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol.

Workup

  1. customat 0°
  2. additionpoured
  3. customThe resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
  4. washThe organic portion was washed with water, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1aae1913fe6347899db787d6b3ea2a7b
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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