Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate → Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-8-[5-fluoro-2-(2-chlorobenzyloxy)phenyl]-oct-7-enoate

HRID 1921881Notes

Reaction equation

HRID 1921881 reaction equation
[Br-].[Cl:2][C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][O:6][C:7]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:8]=1[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:38][C:39]1[CH:40]=[C:41]([CH2:57][CH:58]([CH:68]=O)[CH2:59][CH2:60][CH2:61][CH2:62][C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH:42]=[C:43]([F:56])[C:44]=1[O:45][Si:46]([CH:53]([CH3:55])[CH3:54])([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48]>>[F:38][C:39]1[CH:40]=[C:41]([CH:42]=[C:43]([F:56])[C:44]=1[O:45][Si:46]([CH:47]([CH3:49])[CH3:48])([CH:50]([CH3:52])[CH3:51])[CH:53]([CH3:54])[CH3:55])[CH2:57][CH:58]([CH:68]=[CH:9][C:8]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:7]=1[O:6][CH2:5][C:4]1[CH:34]=[CH:35][CH:36]=[CH:37][C:3]=1[Cl:2])[CH2:59][CH2:60][CH2:61][CH2:62][C:63]([O:65][CH2:66][CH3:67])=[O:64]

Participants

3

Reactant 2

HCID 57971915Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoateHCID 86634289[2-(2-Chlorobenzyloxy)-5-fluorobenzyl]triphenylphosphonium bromide

Product 1

HCID 67493002Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-8-[5-fluoro-2-(2-chlorobenzyloxy)phenyl]-oct-7-enoate

Procedure

Reaction in analogy to Example 21A of [2-(2-chlorobenzyloxy)-5-fluorobenzyl]tri-phenylphosphonium bromide and ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate results in the title compound with 70% of theory as E/Z mixture (2:1).

Sources & evidence

ORD record
ord-e5e760b0d74a4debb2d4a5e744353f82
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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