Tetrahydrofuran → 1,1-Dimethylethyl 4,7,10,13,16-pentaoxaheptadecanoate

HRID 1820583Notes

Reaction equation

HRID 1820583 reaction equation
C[CH:2]([OH:14])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].[CH2:24]1COCC1>[Na]>[C:20]([O:19][C:15](=[O:18])[CH2:16][CH2:17][O:14][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:24])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 15458tert-Butyl acrylateHCID 22182967HCID 22182967, compound

Product 1

HCID 578909091,1-Dimethylethyl 4,7,10,13,16-pentaoxaheptadecanoateYield 79%

Reagents, catalysts & solvents 1

HCID 5360545SodiumCatalyst

Procedure

Methyl tetraethylene glycol (1.0 g, 4.80 mmol) and tert-butyl acrylate (0.308 g, 2.40 mmol) were dissolved in dry THF (10 mL). Sodium metal 0.6 mg, 0.024 mmol) was added to the solution. After stirring for 4 h at room temperature was quenched by the addition of 1 M HCl (15 mL). The quenched reaction mixture was then extracted with CH2Cl2 (1×50 mL, 1×25 mL). The organic layer was dried (MgSO4) and concentrated. After purification by silica gel chromatography (ethyl acetate as eluent), the product was obtained as an oil (1.28 g, 79%).

Workup

  1. customwas quenched by the addition of 1 M HCl (15 mL)
  2. customThe quenched reaction mixture
  3. extractionwas then extracted with CH2Cl2 (1×50 mL, 1×25 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customAfter purification by silica gel chromatography (ethyl acetate as eluent)

Sources & evidence

ORD record
ord-e5a56c44f0b04d04a6a866268c4b797c
Source dataset
uspto-grants-2009_10
Patent number
US07605123B2

Reaction notes

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