Toluene → HCID 86605585, compound

HRID 131291Notes

Reaction equation

[O:1]=[C:2]1[CH:7]=[C:6](CN2CCCC2)[O:5][CH:4]=[C:3]1[O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH3:23][O:24][C:25]([CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:26].[C:47]1(C)C=CC=CC=1>>[CH3:23][O:24][C:25](/[CH:27]=[CH:47]/[C:4]1[O:5][CH:6]=[CH:7][C:2](=[O:1])[C:3]=1[O:14][CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])=[O:26]

Participants

Reactant 3

HCID 1140Toluene

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HCID 86605586HCID 86605586, compound

Product 1

HCID 86605585HCID 86605585, compoundYield 75%

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl [[4-oxo-6-[(1-pyrrolidinyl)methyl]-4H-pyran-3-yl]oxy]acetate (compound obtained in Reference Example 249(2), 12 g) in toluene is added (1-methoxycarbonylmethylidene)triphenylphosphoran (17.36 g) and the mixture is stirred at 60° C. for 3 hours. The reaction mixture is concentrated and the residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=1:1) to give tert-butyl [2-[(1E)-2-(methoxycarbonyl)vinyl]-4-oxo-4H-pyran-3-yl]-oxyacetate (10.99 g, yield; 75%) as colorless crystals. MS (ESI) m/z; 311 [M+H]+, M.p. 115-116° C.

Workup

concentrationThe reaction mixture is concentrated
customthe residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-518c49ac709f4cff96490221587cc406
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384952B2

Reaction notes

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