Ethyl 2-(5,5,6,6,6-pentafluorohexyl)-8-nonenoate → 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylchroman-4-yl]-2-(5,5,6,6,6-pentafluorohexyl)decanoic acid

HRID 1267789Notes

Reaction equation

HRID 1267789 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:28]C=C)[C:10]([C:18]3[CH:23]=[CH:22][C:21]([O:24]COC)=[CH:20][CH:19]=3)([CH2:15][CH2:16][CH3:17])[CH2:11][O:12]2)=[CH:7][CH:6]=1.[F:31][C:32]([F:54])([C:50]([F:53])([F:52])[F:51])[CH2:33][CH2:34][CH2:35][CH2:36][CH:37]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH2:49])[C:38]([O:40]CC)=[O:39]>>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:28][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH:37]([CH2:36][CH2:35][CH2:34][CH2:33][C:32]([F:31])([F:54])[C:50]([F:51])([F:52])[F:53])[C:38]([OH:40])=[O:39])[C:10]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)([CH2:15][CH2:16][CH3:17])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 18546257Ethyl 2-(5,5,6,6,6-pentafluorohexyl)-8-nonenoateHCID 18546265(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)-3-propylchroman

Product 1

HCID 1030466410-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylchroman-4-yl]-2-(5,5,6,6,6-pentafluorohexyl)decanoic acid

Procedure

Starting with (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)-3-propylchroman prepared as in Example 21 and ethyl 2-(5,5,6,6,6-pentafluorohexyl)-8-nonenoate prepared separately, the same procedure as shown in Example 21 was repeated to give 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylchroman-4-yl]-2-(5,5,6,6,6-pentafluorohexyl)decanoic acid.

Workup

  1. customprepared separately

Sources & evidence

ORD record
ord-53c9915ea1e242a2a2cc03ba24422f20
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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