Diethyl Malonate → 11-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)chroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoic acid
Reaction equation
[F:1][C:2]([F:29])([C:19]([F:28])([F:27])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[CH2:3][CH2:4][CH:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[C:6]([O:8]CC)=[O:7].C(OCC)(=O)CC(OCC)=O.BrCCCCCCC=C.ICCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F.[CH2:66]([C:68]1([C:105]2[CH:110]=[CH:109][C:108]([OH:111])=[CH:107][CH:106]=2)[CH:77]([CH2:78]CCCCCCCCC(CCCCCCC(F)(F)C(F)(F)F)C(O)=O)[C:76]2[C:71](=[CH:72][C:73]([OH:104])=[CH:74][CH:75]=2)[O:70][CH2:69]1)[CH3:67]>>[CH2:66]([C:68]1([C:105]2[CH:106]=[CH:107][C:108]([OH:111])=[CH:109][CH:110]=2)[CH:77]([CH2:78][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:5]([CH2:4][CH2:3][C:2]([F:29])([F:1])[C:19]([F:27])([F:28])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[C:6]([OH:8])=[O:7])[C:76]2[C:71](=[CH:72][C:73]([OH:104])=[CH:74][CH:75]=2)[O:70][CH2:69]1)[CH3:67]Participants
6
Reactant 5
Product 1
Procedure
Starting with the ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoate prepared from diethyl malonate, 8-bromo-1-octene and 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane as in Example 5 and the allyl compound prepared in Example 21, the same procedure as shown in Example 21 was repeated to give 11-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)chroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoic acid.
Sources & evidence
- ORD record
- ord-9eba46ed96804efbab7302b671c17308
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552068B1
Reaction notes
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