3,4-dihydro-2H-pyran → 2-(2-Fluoro-5-nitro-benzyloxy)-tetrahydro-pyran

HRID 1796628Notes

Reaction equation

HRID 1796628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][OH:12].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][O:12][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:13]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 4437169(2-Fluoro-5-nitrophenyl)methanol

Product 1

HCID 221796312-(2-Fluoro-5-nitro-benzyloxy)-tetrahydro-pyranYield 70.1%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 394A (1.8 g, 10.5 mmol) in CH2Cl2 (10 ml) was added dihydropyran (1.94 ml, 21.2 mmol) and PPTS (150 mg, 0.60 mmol). The reaction was stirred at rt overnight, washed with brine, concentrated, purified by silica gel flash column chromatography to give 394B (1.88 g, 70%) (100% CH2Cl2).

Workup

  1. washwashed with brine
  2. concentrationconcentrated
  3. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-4b017ca62dfd46dfa1179d30b2299564
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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