10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoic acid → 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid

HRID 1267787Notes

Reaction equation

HRID 1267787 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]CCCC(CCCC(F)(F)C(F)(F)F)C(O)=O)[C:7]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)([CH2:12][CH2:13][CH3:14])[CH2:8][S:9]2)=[CH:4][CH:3]=1.[F:44][C:45]([F:71])([C:61]([F:70])([F:69])[C:62]([F:68])([F:67])[C:63]([F:66])([F:65])[F:64])[CH2:46][CH2:47][CH:48]([CH2:54][CH2:55][CH2:56]CCC=C)[C:49]([O:51]CC)=[O:50]>>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:56][CH2:55][CH2:54][CH:48]([CH2:47][CH2:46][C:45]([F:44])([F:71])[C:61]([F:70])([F:69])[C:62]([F:67])([F:68])[C:63]([F:64])([F:65])[F:66])[C:49]([OH:51])=[O:50])[C:7]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)([CH2:12][CH2:13][CH3:14])[CH2:8][S:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1021140610-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoic acidHCID 12048018Ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-8-nonenoate

Product 1

HCID 1019040610-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid

Procedure

Starting with the allyl compound prepared in Example 29 and ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-8-nonenoate prepared separately, the same procedure as shown in Example 13 was repeated to give 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoic acid.

Workup

  1. customprepared separately

Sources & evidence

ORD record
ord-4aa33bfed30149e984d58873c4d708d8
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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