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

HRID 2180521Notes

Reaction equation

HRID 2180521 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:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27]([CH:35]([CH3:37])[CH3:36])=[CH:28][C:29]([CH3:34])([CH3:33])[O:30]2)=[CH:25][C:24]=1/[C:38](/[CH3:43])=[C:39](/[F:42])\[CH:40]=O)[CH2:19][CH2:20][CH3:21]>>[CH2:18]([O:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27]([CH:35]([CH3:36])[CH3:37])=[CH:28][C:29]([CH3:33])([CH3:34])[O:30]2)=[CH:25][C:24]=1/[C:38](/[CH3:43])=[C:39](/[F:42])\[CH:40]=[CH:9]\[C:10](\[CH3:17])=[CH:11]\[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 6000084Ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoateHCID 22490854(2E)-3-(7-Butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enal2×

Product 1

HCID 86759710ethyl (2E,4E,6E)-7-(7-butoxy-4-isopropyl-2,2-dimethyl-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 (183 mg, 0.70 mmol) and (2E)-3-(7-butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enal (Compound 100, 86 mg, 0.24 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-3e7f77a5975c4e5c836f9860047e58fa
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…