Hydrochloric Acid → HCID 44622260, compound

HRID 876202Notes

Reaction equation

HRID 876202 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14].[Na].Cl>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:14][CH2:13][C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8178Triethylene glycol monomethyl etherHCID 15458tert-Butyl acrylateHCID 5360545Sodium

Product 1

HCID 44622260HCID 44622260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylene glycol monomethyl ether (1.0 g, 6.1 mmol) and tert-butyl acrylate (390 mg, 3.05 mmol) were dissolved in dry THF and sodium metal (0.7 mg, 0.03 mmol) was added at room temperature. The mixture was stirred for 4 hours and 1 M HCl was added to quench the reaction. The mixture was extracted twice with dichloromethane, and the organic phase was dried over MgSO4 and concentrated in vacuo to provide an oil, which was purified by silica chromatography using ethyl acetate as eluent. The product was an oil, 773 mg (44%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted twice with dichloromethane
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto provide an oil, which
  7. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-b3a744d8a9ed4fdbb52b63e77b2e7115
Source dataset
uspto-grants-2015_03
Patent number
US08987197B2

Reaction notes

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