Oxygen → 4-(1-methoxytridecyl)-5-hydroxy-2(5H)-furanone

HRID 488208

Reaction equation

HRID 488208 reaction equation
CO[CH:3]([C:16]1C=C([Si](C)(C)C)O[CH:20]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]CCCCCC.C1C(I)=C(O)C(I)=C2OC3C([C:41]4([O:54][C:52](=[O:53])[C:43]5[C:44](Cl)=[C:45](Cl)[C:46](Cl)=[C:47](Cl)[C:42]4=5)C=12)=CC(I)=C(O)C=3I.[O:58]=O.[O:60]1[CH2:64]CCC1>>[CH3:64][O:60][CH:44]([C:43]1[CH:52]([OH:53])[O:54][C:41](=[O:58])[CH:42]=1)[CH2:45][CH2:46][CH2:47][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:16][CH3:20]

Participants

5

Reactant 4

HCID 977OxygenHCID 8028TetrahydrofuranHCID 69439Rose Bengal LactoneHCID 150370584-(1-Methoxytridecyl)-2-trimethylsilylfuran

Product 1

HCID 150370594-(1-methoxytridecyl)-5-hydroxy-2(5H)-furanone

Procedure

A mixture of 4-(1-methoxytridecyl)-2-trimethylsilylfuran (280 mg, 0.8 mmol) and Rose Bengal (5 mg) in tetrahydrofuran (7 ml) was exposed to singlet oxygen for 5 hours at -78 degrees. The residue, after solvent removal, was flash chromatographed on silica using 60% ethyl ether/petroleum ether. Fractions with Rf of about 0.21 on evaporation afforded the 4-(1-methoxytridecyl)-5-hydroxy-2(5H) -furanone as a colorless prism: mp 53-4 degrees.

Workup

  1. customThe residue, after solvent removal
  2. customchromatographed on silica using 60% ethyl ether/petroleum ether
  3. customFractions with Rf of about 0.21 on evaporation

Sources & evidence

ORD record
ord-4428c2ebb73443eaa8a71ae1c841d243
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Linked notes

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