Ethylene Glycol → (4-[1,3]Dioxolan-2-yl-2-fluorophenoxy)triisopropylsilane

HRID 130982Notes

Reaction equation

HRID 130982 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:5]=[O:6].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[O:6]1[CH2:21][CH2:22][O:23][CH:5]1[C:4]1[CH:7]=[CH:8][C:9]([O:10][Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 597300273-Fluoro-4-triisopropylsilanyloxybenzaldehyde

Product 1

HCID 59730094(4-[1,3]Dioxolan-2-yl-2-fluorophenoxy)triisopropylsilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 5 L 3-neck flask equipped with a condenser and a Dean-Stark trap add 3-fluoro-4-triisopropylsilanyloxybenzaldehyde (Example 737, Part A) (90.14 g, 0.3041 mol), ethylene glycol (188.75 g, 3.041 mol), and p-toluenesulfonic acid (0.58 g, 0.003041 mol) in toluene (3.155 L). Beat to boil and reflux until 130 mL of H2O (lower layer) is collected in the Dean-Stark trap (5 hrs). Cool to room temperature, wash with 10% aqueous potassium carbonate solution (2×1 L) and brine (2×1 L), and dry over sodium sulfate. Filter and concentrate to give the crude product.

Workup

  1. customInto a 5 L 3-neck flask equipped with a condenser
  2. customis collected in the Dean-Stark trap (5 hrs)
  3. washwash with 10% aqueous potassium carbonate solution (2×1 L) and brine (2×1 L)
  4. dry with materialdry over sodium sulfate
  5. filtrationFilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-b6bdca7ca7a9468c90552d8389196b00
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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