Potassium Carbonate → 1,1,1-Triphenyl-1-sila-2-butene-4-ol

HRID 1004750

Reaction equation

HRID 1004750 reaction equation
[C:1]1([Si:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:9][CH2:10][O:11]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]1([Si:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[CH:9][CH2:10][OH:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 538005221,1,1-Triphenyl-4-acetoxy-1-sila-2-butene

Product 1

HCID 543215981,1,1-Triphenyl-1-sila-2-butene-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude acetoxy compound from Example 14 is dissolved in 250 mL methanol, and 25.0 g of potassium carbonate is added all at once. After stirring for 2 hours, the reaction mixture is filtered and concentrated. The concentrated residue is partitioned between 200/200 mL water/ethyl acetate. The organic layer is removed, washed with brine, dried and concentrated. The crude material is purified by flash chromatography using silica gel to afford the pure product.

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationconcentrated
  3. customThe concentrated residue is partitioned between 200/200 mL water/ethyl acetate
  4. customThe organic layer is removed
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe crude material is purified by flash chromatography
  9. customto afford the pure product

Sources & evidence

ORD record
ord-83fe3df37f3c4383a976cf5db27735ce
Source dataset
uspto-grants-2000_04
Patent number
US06051699

Linked notes

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