Pentaerythritol → HCID 18412816, compound

HRID 992591Notes

Reaction equation

HRID 992591 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[Si:10](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1C=CC=CC=1)[C:11]1C=CC=CC=1>N1C=CC=CC=1.CCOC(C)=O>[OH:1][CH2:2][C:3]([CH2:8][O:9][Si:10]([CH3:17])([CH3:11])[C:23]([CH3:26])([CH3:25])[CH3:24])([CH2:6][OH:7])[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 8285PentaerythritolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 18412816HCID 18412816, compoundYield 133.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent3×

Procedure

Pentaerythritol [2,2-bis(hydroxymethyl)propane-1,3-diol] (10.55 g, 77 mmol) was taken up in 100 mL of dry pyridine. Tert-butyldiphenylsilyl chloride (4.26 g, 15 mmol, 0.2 eq) was then added dropwise over 10 minutes to the pyridine solution at ambient temperature. The reaction mixture was stirred at ambient temperature for 24 hours at which point TLC (EtOAc) indicated that the reaction was complete. The reaction was worked-up by diluting the reaction mixture with 250 mL of EtOAc and washing the organic layer with 10% HCl (3×200 mL). The organic layer was dried over sodium sulfate and then concentrated in vacuo to afford a thick pale yellow oil. Column chromatography on 200 g of silica gel eluting with EtOAc followed by concentration of the appropriate fractions afforded 5.01 g of the product as a clear colorless oil which solidified very slowly upon standing (86%). 1H NMR (CDCl3, 300 MHz): δ1.08 (s, 9H), 3.66 (s, 2H), 3.74 (s, 6H), 7.42 (m, 6H), 7.65 (m, 4H); MS (70 eV, EI) 392 (M+NH4)+.

Workup

  1. washwashing the organic layer with 10% HCl (3×200 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford a thick pale yellow oil

Sources & evidence

ORD record
ord-0de1ccb9aac14e119f9fefd5f83a5f8a
Source dataset
uspto-grants-2002_10
Patent number
US06469065B1

Reaction notes

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