Pentaerythritol → HCID 15257095, compound

HRID 270756Notes

Reaction equation

HRID 270756 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]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1.CCOC(C)=O>[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][O:7][Si:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]([CH3:26])([CH3:24])[CH3:25])[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 8285PentaerythritolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 15257095HCID 15257095, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

2,2-bis(hydroxymethyl)propane-1,3-diol (10.55 g, 77 mmole) was taken up in dry pyridine (100 mL). Tert-butyldiphenylsilyl chloride (4.26 g, 15 mmole, 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. TLC (EtOAc) indicated that the reaction was complete. The reaction was diluted with EtOAc (250 mL), washed 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 silica gel (200 g), eluted with EtOAC followed by concentration of the appropriate fractions gave 5.01 g of the title compound as a clear colorless oil which solidified very slowly upon standing (86%). 1H NMR (300 MHz, CDCl3) 7.65 (m, 4H), 7.42 (m, 6H), 3.74 (s, 6H), 3.66 (s, 2H), 1.08 (s, 9H); MS (70 eV, EI) 392 (M+NH4)+.

Workup

  1. washwashed 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
  5. washColumn chromatography on silica gel (200 g), eluted with EtOAC

Sources & evidence

ORD record
ord-f9e22f041cbc4a00a6380d9ec159feb0
Source dataset
uspto-grants-2008_11
Patent number
US07449595B2

Reaction notes

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