Tetrahydrofuran → 1,1-Dimethylethyl 4,7,10,13,16,19,22-heptaoxatricosanoate

HRID 1044635Notes

Reaction equation

HRID 1044635 reaction equation
C[CH:2]([OH:20])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19].[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[CH:22]=[CH2:23].[CH2:30]1COCC1>[Na]>[C:26]([O:25][C:21](=[O:24])[CH2:22][CH2:23][O:20][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:30])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 15458tert-Butyl acrylateHCID 86587580HCID 86587580, compound

Product 1

HCID 578909031,1-Dimethylethyl 4,7,10,13,16,19,22-heptaoxatricosanoateYield 58%

Reagents, catalysts & solvents 1

HCID 5360545SodiumCatalyst

Procedure

Methyl hexaethylene glycol (1.0 g, 3.37 mmol) and tert-butyl acrylate (0.216 g, 1.69 mmol) were dissolved in dry THF (10 mL). Sodium metal 0.4 mg, 0.016 mmol) was added to the solution. After stirring for 4 h at room temperature, the reaction mixture 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 (0.832 g, 58%).

Workup

  1. customthe reaction mixture was 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-c6b8e7c045604cbe833ddc0cd9a9614c
Source dataset
uspto-grants-2013_10
Patent number
US08563685B2

Reaction notes

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