Diethyl Ether → 1-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane

HRID 329789Notes

Reaction equation

HRID 329789 reaction equation
[C:1]([O:9][CH2:10][CH:11]([CH3:14])[CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[C:1]([O:9][CH2:10][CH:11]([CH3:14])[CH2:12][O:13][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80803,4-dihydro-2H-pyran2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 14796046Benzoic acid 3-hydroxy-2-methyl-propyl ester

Product 1

HCID 147960471-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropaneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-benzoyloxy-2-methylpropanol (369 mg; 1.9 mmol), dihydropyran (273 mg; 3.25 mmol) and pyridinium p-toluenesulfonate (50 mg; 0.2 mmol) in anhydrous dichloromethane (10 ml) was stirred at room temperature for 2 hours. Dihydropyran (200 mg; 2.38 mmol) and pyridinium p-toluenesulfonate (50 mg; 0.2 mmol) were further added thereto, and the resultant mixture was stirred for 3 hours. Ether (50 ml) was added to the reaction mixture, which was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was purified by TLC using a mixture of ethyl acetate and benzene (1:4) to give 1-benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane (466.3 mg; yield, 88%).

Workup

  1. washwas washed with an aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customthe residue was purified by TLC
  5. additiona mixture of ethyl acetate and benzene (1:4)

Sources & evidence

ORD record
ord-a7c1850279a74faf82a52536d9c9bf90
Source dataset
uspto-grants-1990_01
Patent number
US04892961

Reaction notes

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