Ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoate → ethyl (2E,4E,6E)-7-(7-ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoate

HRID 2180522Notes

Reaction equation

HRID 2180522 reaction equation
C(OP([CH2:9]/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:18]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:26][C:27]([CH3:32])([CH3:31])[O:28]2)=[CH:23][C:22]=1/[C:39](/[CH3:44])=[C:40](/[F:43])\[CH:41]=O)[CH3:19]>>[CH2:18]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:26][C:27]([CH3:32])([CH3:31])[O:28]2)=[CH:23][C:22]=1/[C:39](/[CH3:44])=[C:40](/[F:43])\[CH:41]=[CH:9]\[C:10](\[CH3:17])=[CH:11]\[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:19]

Participants

3

Reactant 2

HCID 6000084Ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoateHCID 22490763(2E)-3-(7-Ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-2-fluoro-but-2-enal2×

Product 1

HCID 86759711ethyl (2E,4E,6E)-7-(7-ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoate

Procedure

Following General Procedure O, ethyl 4-(diethoxyphosphoryl)-3-methyl-but-2E-enoate (237 mg, 0.90 mmol) and (2E)-3-(7-ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-2-fluoro-but-2-enal (Compound 101, 113 mg, 0.31 mmol) were reacted to give the title compound as a yellow oil after purification by flash chromatography (silica gel, 5% ethyl acetate in hexane).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a906f3239abe4e49aa70722a6531a483
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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