(3-Carboxypropyl)(triphenyl)phosphanium bromide → (e)-5-{5-[2-(3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenyl)ethyl]-2-thienyl}-4-heptenoic acid

HRID 49338Notes

Reaction equation

HRID 49338 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[S:31][C:30]([C:32](=O)[CH2:33][CH3:34])=[CH:29][CH:28]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br-].[C:37]([CH2:40]CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:39])=[O:38].[CH3:62][C:63](C)([O-])C.[K+]>>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[S:31][C:30](/[C:32](/[CH2:62][CH3:63])=[CH:33]/[CH2:34][CH2:40][C:37]([OH:39])=[O:38])=[CH:29][CH:28]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideHCID 206362861-{5-[2-(3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 69825231(e)-5-{5-[2-(3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenyl)ethyl]-2-thienyl}-4-heptenoic acid

Procedure

In a manner similar to that of Example 6(i), by reaction of 5.08 g (9.5 mmol) of 1-{5-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone with 6.1 g (14 mmol) of (3-carboxypropyl)triphenylphosphonium bromide and 3.1 g (28 mmol) of potassium tert-butoxide, the desired product is obtained in the form of a yellow oil (m=2.7 g; Y=48%).

Sources & evidence

ORD record
ord-4b74ece7c24142998258a00b71333e48
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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