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-(5,5,6,6,6-pentafluorohexyl)decanoic acid

HRID 1267786Notes

Reaction equation

HRID 1267786 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][CH2:27][CH2:28][CH2:29][CH:30]([CH2:34][CH2:35]CC(F)(F)C(F)(F)F)[C:31]([OH:33])=[O:32])[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:67])([C:63]([F:66])([F:65])[F:64])[CH2:46][CH2:47]CCC(CCCCCC=C)C(OCC)=O>>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH2:34][CH2:35][CH2:47][CH2:46][C:45]([F:67])([F:44])[C:63]([F:66])([F:65])[F:64])[C:31]([OH:33])=[O:32])[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

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 18546257Ethyl 2-(5,5,6,6,6-pentafluorohexyl)-8-nonenoate

Product 1

HCID 1016836810-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylthiochroman-4-yl]-2-(5,5,6,6,6-pentafluorohexyl)decanoic acid

Procedure

Starting with the allyl compound prepared in Example 29 and ethyl 2-(5,5,6,6,6-pentafluorohexyl)-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-(5,5,6,6,6-pentafluorohexyl)decanoic acid.

Workup

  1. customprepared separately

Sources & evidence

ORD record
ord-ae59b85212b542d38f13af00c0b71237
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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