Triethylamine → HCID 19363564, compound

HRID 850331Notes

Reaction equation

HRID 850331 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])=[CH:5][CH:4]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][O:13][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11458789HCID 11458789, compound

Product 1

HCID 19363564HCID 19363564, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Combine 4-(p-methoxybenzyloxy)-1,2-butandiol (42.43 g, 187.5 mmol) with DMF (700 mL) and cool in an ice bath before adding t-butyldimethylsilyl chloride (31.1 g, 206 mmol), triethylamine (31.4 mL, 225 mmol), and 4-dimethylaminopyridine (5.8 g, 47 mmol). Stir the mixture in the ice bath for 5 minutes and then allow to warm to ambient temperature and stir for sixteen hours. Filter and wash the filter cake with diethyl ether. Separate the aqueous layer and extract twice with ether. Combine the organic layers extract with water and saturated sodium chloride solution, dry over MgSO4, filter and concentrate in vacuo. Chromatograph on silica gel eluting with 2/8 ethyl acetate/hexane to give 51.4 g of the title compound the as an oil. Rf =0.25; silica gel, 2/8 ethyl acetate/hexane.

Workup

  1. filtrationFilter
  2. washwash the filter cake with diethyl ether
  3. customSeparate the aqueous layer
  4. extractionextract twice with ether
  5. extractionextract with water and saturated sodium chloride solution
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-16c067020ac34d5e92cc4ae0909373c1
Source dataset
uspto-grants-2000_01
Patent number
US06017923

Reaction notes

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