Ethyl vinyl ether → HCID 66730438, compound

HRID 1959975Notes

Reaction equation

HRID 1959975 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C@@H:12]1[CH2:16][O:15][CH2:14][C@H:13]1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([O:20][CH2:21]C)=[CH2:19].C(N(CC)CC)C>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C@H:12]1[C@H:13]([O:17][CH2:21][O:20][CH2:18][CH3:19])[CH2:14][O:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 8471TriethylamineHCID 66730516HCID 66730516, compound2×

Product 1

HCID 66730438HCID 66730438, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

Trans-4-[2-(benzyloxy)ethoxy]tetrahydrofuran-3-ol (2.20 g, 9.23 mmol) synthesized in (18a), ethyl vinyl ether (3.33 g, 46.2 mmol), and pyridinium paratoluene sulfonate (231 mg, 0.92 mmol) were dissolved in dichloromethane (22 ml), followed by stirring at room temperature for one hour. Triethylamine (187 mg, 1.84 mmol) was then added, and the resulting mixture was directly purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V) to give trans-3-[2-(benzyloxy)ethoxy]-4-(ethoxymethoxy)tetrahydrofuran (2.88 g, yield 100%). This compound (1.55 g, 5.00 mmol) was dissolved in methanol (30 ml), to which 20% palladium hydroxide-carbon (155 mg) was added, followed by stirring at room temperature for one hour under a hydrogen atmosphere. The resulting solution was concentrated under reduced pressure to give the desired title compound (725 mg, yield 98%).

Workup

  1. customthe resulting mixture was directly purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V)

Sources & evidence

ORD record
ord-5f45e734a5e3456fb1f11f76ca5506b8
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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