Diethyl Malonate → 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)chroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid
Reaction equation
[F:1][C:2]([F:28])([C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH2:3][CH2:4][CH:5]([CH2:11]CCCCC=C)[C:6]([O:8]CC)=[O:7].C(OCC)(=O)CC(OCC)=O.ICCCCCC=C.ICCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F.[CH2:64]([C:66]1([C:103]2[CH:108]=[CH:107][C:106]([OH:109])=[CH:105][CH:104]=2)[CH:75]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82]CCC(CCCCCCC(F)(F)C(F)(F)F)C(O)=O)[C:74]2[C:69](=[CH:70][C:71]([OH:102])=[CH:72][CH:73]=2)[O:68][CH2:67]1)[CH3:65]>>[CH2:64]([C:66]1([C:103]2[CH:104]=[CH:105][C:106]([OH:109])=[CH:107][CH:108]=2)[CH:75]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:11][CH:5]([CH2:4][CH2:3][C:2]([F:1])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:22])([F:21])[F:23])[C:6]([OH:8])=[O:7])[C:74]2[C:69](=[CH:70][C:71]([OH:102])=[CH:72][CH:73]=2)[O:68][CH2:67]1)[CH3:65]Participants
6
Reactant 5
Product 1
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 21, the same procedure as shown in Example 21 was repeated to give 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)chroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid.
Sources & evidence
- ORD record
- ord-a190712b8a4943cb83b6a16ea9ba0b2e
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552068B1
Reaction notes
Loading…