3,4-dihydro-2H-pyran → 8-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one

HRID 2099388

Reaction equation

HRID 2099388 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S([O-])(=O)=O)=[CH:9][CH:8]=1.[NH+]1C=C[CH:21]=[CH:20][CH:19]=1.[Cr](Cl)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[C:35]([O-])(=[O:37])C.[Na+]>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:37][CH2:35][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:17](=[O:25])[CH2:21][CH2:20][CH2:19]2

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 517045Sodium AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 219860898-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-oneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The diol (Intermediate H3) (2.42 g, 13.5 mmol) was dissolved in CH2Cl2 (75 mL) and reacted with dihydropyran (1.3 mL, 13.8 mmol) and pyridinium para-toluene sulfonate (PPTS) (350 mg, 1.36 mmol) at rt for 18 h. The mixture was concentrated onto SiO2 and purified by chromatography with 10% EtOAc:Hx. The tetrahydropyranyl (THP) protected alcohol (2.02 g, 7.70 mmol) was dissolved in CH2Cl2 (10 mL) and added to a mixture of pyridinium chlorochromate (PCC) (4.9 g, 22.2 mmol), sodium acetate (310 mg, 3.56 mmol) and celite (110 g) in CH2Cl2 (100 mL). The mixture was reacted at rt for 18 h and filtered through celite. The residue was purified by chromatography on SiO2 with 20 to 30% EtOAc:Hx to yield 8-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one (Intermediate H4) (˜55%).

Workup

  1. concentrationThe mixture was concentrated onto SiO2
  2. custompurified by chromatography with 10% EtOAc
  3. customThe mixture was reacted at rt for 18 h
  4. filtrationfiltered through celite
  5. customThe residue was purified by chromatography on SiO2 with 20 to 30% EtOAc

Sources & evidence

ORD record
ord-f6c33da865724e7bb937be9df4336487
Source dataset
uspto-grants-2009_08
Patent number
US07569584B2

Linked notes

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