Diethyl Ether → 4H-Furo[3,2-c][l]benzopyran-2,3-dione

HRID 1607920Notes

Reaction equation

C[Si](C)(C)[O:3][C:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH:5]=1.CC[O:18][CH2:19][CH3:20].C([O:24]C(C)C)(C)C>>[O:3]1[C:4]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6][C:5]=2[C:19](=[O:18])[C:20]1=[O:24]

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 7914Diisopropyl Ether

HCID 11379020Silane, (2H-1-benzopyran-4-yloxy)trimethyl-

Product 1

HCID 142560214H-Furo[3,2-c][l]benzopyran-2,3-dioneYield 86%

Procedure

To a stirred solution of 4-[(trimethylsilyl)oxy]-2H-1-benzopyran (L. H. Hellberg, and A. Zuarez, Tetrahedron Letters, 40, 3553 (1974)) (205.8 g, 0.917 mole) in anhydrous ether (600 ml) oxalyl chloride (58.2 g, 0.458 mole) is added dropwise over a period of 40 minutes at room temperature under nitrogen. The suspension is stirred at room temperature for 18 hoursand then diluted with isopropyl ether (~300 ml). The precipitate is collected by filtration and washed with isopropyl ether to give 80.2 g (86%) of orange-red solid, mp 146°-8° C. Recrystallization from tetrahydrofuranisopropyl ether gives an analytical sample, mp 146°-148° C.

Workup

filtrationThe precipitate is collected by filtration
washwashed with isopropyl ether

Sources & evidence

ORD record: ord-8b47dbb437e3410cb3e5fb4124bbda58
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04868199

Reaction notes

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