3,4-dihydro-2H-pyran → HCID 21836595, compound

HRID 1379828Notes

Reaction equation

HRID 1379828 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:5][CH:4]=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl.C(OCC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 21836649(2'-Nitro[1,1'-biphenyl]-4-yl)methanol

Product 1

HCID 21836595HCID 21836595, compoundYield 106.5%

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-hydroxymethyl-2'-nitro-1,1'-biphenyl (3.06 g, 13.4 mmol) and 3,4-dihydropyran (1.8 mL, 20.1 mmol) in methylene chloride (50 mL) under a nitrogen atmosphere was treated with pyridinium p-toluenesulfonate (336 mg, 1.34 mmol). After stirring for 3 hours at room temperature, thin layer chromatography indicated that no starting material remained. The reaction mixture was diluted with ethyl ether (300 mL). The ether extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum and the residue purified by preparative high pressure liquid chromatography on silica gel, eluting with hexane/ethyl acetate (10:1) to give 4.47 g of the product.

Workup

  1. washThe ether extracts were washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customthe residue purified by preparative high pressure liquid chromatography on silica gel
  6. washeluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-294c6cee31114d919341d767fb30314d
Source dataset
uspto-grants-1997_09
Patent number
US05672596

Reaction notes

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