Formaldehyde → HCID 68937051, compound

HRID 388747Notes

Reaction equation

HRID 388747 reaction equation
[C:1]([Si:5]([O:8][C@@H:9]1[CH2:14][C@@H:13]([O:15][Si](CC)(CC)CC)[CH2:12][CH:11]=[C:10]1[CH2:23]I)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[In].[CH2:26]=[O:27]>O.O1CCCC1>[Si:5]([O:8][C@H:9]1[C:10](=[CH2:23])[C@H:11]([CH2:26][OH:27])[CH2:12][C@H:13]([OH:15])[CH2:14]1)([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5359967Indium2×HCID 68940022HCID 68940022, compound

Product 1

HCID 68937051HCID 68937051, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 16G (2.5 g, 5.2 mmol) was dissolved in 20 mL of water and 30 mL of tetrahydrofuran. Indium powder (0.90 g) was added followed by formaldehyde (37% aqueous solution, 1.6 mL, 21 mmol). Two additional portions of indium (0.3 g each) were added to drive the reaction toward completion. The reaction was diluted with 180 mL of water and extracted twice with 250 mL each of ethyl acetate. The combined organic layers were washed sequentially with 5% NaHCO3 and brine, then dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (200 mL of SiO2, elution with a gradient of 1:1 to 3:1 ethyl acetate:hexanes) afforded the titled compound (0.97 g, 68%).

Workup

  1. customthe reaction toward completion
  2. extractionextracted twice with 250 mL each of ethyl acetate
  3. washThe combined organic layers were washed sequentially with 5% NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography (
  8. wash200 mL of SiO2, elution with a gradient of 1:1 to 3:1 ethyl acetate

Sources & evidence

ORD record
ord-0ed958ebc33247149da2076e1b114ad3
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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