Diethyl Malonate → 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid

HRID 1267782Notes

Reaction equation

HRID 1267782 reaction equation
FC(F)(C(F)(F)C(F)(F)C(F)(F)F)CCC(CCCCCC=C)C(OCC)=O.C(OCC)(=O)CC(OCC)=O.ICCCCCC=C.I[CH2:49][CH2:50][C:51]([F:63])([F:62])[C:52]([F:61])([F:60])[C:53]([F:59])([F:58])[C:54]([F:57])([F:56])[F:55].[CH2:64]([C:66]1([C:102]2[CH:107]=[CH:106][C:105]([OH:108])=[CH:104][CH:103]=2)[CH:75]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH:84](CCCCCCC(F)(F)C(F)(F)F)[C:85]([OH:87])=[O:86])[C:74]2[C:69](=[CH:70][C:71]([OH:101])=[CH:72][CH:73]=2)[S:68][CH2:67]1)[CH3:65]>>[CH2:64]([C:66]1([C:102]2[CH:103]=[CH:104][C:105]([OH:108])=[CH:106][CH:107]=2)[CH:75]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH:84]([CH2:49][CH2:50][C:51]([F:63])([F:62])[C:52]([F:61])([F:60])[C:53]([F:59])([F:58])[C:54]([F:57])([F:56])[F:55])[C:85]([OH:87])=[O:86])[C:74]2[C:69](=[CH:70][C:71]([OH:101])=[CH:72][CH:73]=2)[S:68][CH2:67]1)[CH3:65]

Participants

6

Reactant 5

HCID 7761Diethyl MalonateHCID 748871,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexaneHCID 106328827-Iodohept-1-eneHCID 12048018Ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-8-nonenoateHCID 1854627710-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acid

Product 1

HCID 1021220810-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid

Procedure

Starting with the ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-8-nonenoate prepared from diethyl malonate, 7-iodo-1-heptene and 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane as in Example 9 and the allyl compound prepared in Example 13, the same procedure as shown in Example 13 was repeated to give 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid.

Sources & evidence

ORD record
ord-967a807ca45a4bd0b330dad73195ccb6
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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