Diethyl Ether → HCID 15504481, compound

HRID 2380837Notes

Reaction equation

HRID 2380837 reaction equation
[OH:1][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.C(OCC)C>ClCCl>[CH3:8][C:2]([O:1][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][O:27]1)([CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6653Ethyl 2-hydroxyisobutyrateHCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Product 1

HCID 15504481HCID 15504481, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-hydroxy-2-methylpropanoate (5.20 mL, 38.06 mmol) in dichloromethane (100 mL) were sequentially added pyridine 4-methylbenzenesulfonate (1.0 g, 3.80 mmol) and 3,4-dihydro-2H-pyran (5.20 ml, 57.0 mmol). The resulting mixture was stirred at room temperature overnight. Ethyl ether was added (600 mL) and the resulting organic layer was washed with brine (3×100 ml), dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give the title compound (7.85 g, 95%).

Workup

  1. washthe resulting organic layer was washed with brine (3×100 ml)
  2. dry with materialdried over anhydrous sodium sulphate
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1fd5fb08a06c4fcea88d5fa98c058dd3
Source dataset
uspto-grants-2012_09
Patent number
US08258122B2

Reaction notes

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