Ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoate → 11-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylchroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoic acid

HRID 1267790Notes

Reaction equation

HRID 1267790 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][CH:36]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH2:49])[C:37]([O:39]CC)=[O:38]>>[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][CH2:42][CH:36]([CH2:35][CH2:34][CH2:33][C:32]([F:31])([F:54])[C:50]([F:51])([F:52])[F:53])[C:37]([OH:39])=[O:38])[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 12043786Ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoateHCID 18546265(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)-3-propylchroman

Product 1

HCID 1021136611-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylchroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoic acid

Procedure

Starting with (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)-3-propylchroman prepared as in Example 21 and ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoate prepared separately, the same procedure as shown in Example 21 was repeated to give 11-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-propylchroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoic acid.

Workup

  1. customprepared separately

Sources & evidence

ORD record
ord-ce87cb004cac4825a48010588807c2e1
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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