Tetrahydrofuran → Pyren-1(2H)-one

HRID 1355613Notes

Reaction equation

HRID 1355613 reaction equation
CO[CH:3]=[CH:4][C:5]([O:7][Si](C)(C)C)=[CH2:6].[CH2:12]1[CH2:16]O[CH2:14][CH2:13]1>[Cl-].[Cl-].[Zn+2]>[C:5]1(=[O:6])[C:7]2[C:16]3=[C:16]4[C:4](=[CH:5][CH:6]=2)[CH:3]=[CH:14][CH:13]=[C:12]4[CH:14]=[CH:13][C:12]3=[CH:3][CH2:4]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadiene

Product 1

HCID 53437953Pyren-1(2H)-one

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To the 7,24-bis-OSiMe3-protected 1″,2″-dihydro-3″-aldehyde (1″,2″-dihydro-Intermediate II, 30 mg) in THF (0.8 μL) at rt was added 1-methoxy-3-trimethylsilyloxy-butadiene (50 μL) followed by ZnCl2 (80 μL, 1M solution in Et2O) After 2 h at rt and 12 h at 0° C., bis-protected Diels-Alder adducts were obtained without workup by PTLC on silica gel (1×1000 μm plate) using 2/8 acetone/hexanes as eluant. The pure products (7 mg methoxy-substituted pyranone and 10 mg pyrenone) thus obtained were characterized by 1H NMR. Both products were deprotected separately as described previously (10 mg pyrenone yielded 9 mg deprotected product and 7 mg methoxypyranone yielded 6 mg deprotected product). The deprotected products were characterized by 1H NMR.

Workup

  1. custombis-protected Diels-Alder adducts were obtained without workup by PTLC on silica gel (1×1000 μm plate)

Sources & evidence

ORD record
ord-f101e297704e40358efbfe1b51a8c0d8
Source dataset
uspto-grants-2003_07
Patent number
US06586452B1

Reaction notes

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