Hexafluoroacetone → HCID 87504064, compound

HRID 644579Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:33](/[CH2:37][CH3:38])=[CH:34]/[C:35]#[CH:36])[CH:30]=[CH:31][CH:32]=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].C([Li])CCC.[F:44][C:45]([F:53])([F:52])[C:46]([C:48]([F:51])([F:50])[F:49])=[O:47]>>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:33](/[CH2:37][CH3:38])=[CH:34]/[C:35]#[C:36][C:46]([C:48]([F:51])([F:50])[F:49])([OH:47])[C:45]([F:53])([F:52])[F:44])[CH:30]=[CH:31][CH:32]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 12695Hexafluoroacetone

HCID 87504004HCID 87504004, compound

HCID 178418339Butyllithium

Product 1

HCID 87504064HCID 87504064, compound

Procedure

In a manner analogous to example 21, by reaction of 5 g (9.1 mmol) of (E)-1-(3-{2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)-phenyl]ethyl}phenyl)-1-ethyl-but-1-en-3-yne with 4 ml (10 mmol) of a 2.5 M solution of butyllithium and a flow of hexafluoroacetone. The desired product is obtained in the form of a yellow oil (m=3.7 g; Y=57%).

Sources & evidence

ORD record: ord-07e8cbee77a641479ec771ec93ca284d
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700657B2

Reaction notes

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