Hexafluoroacetone → (e)-6-{5-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-2-thienyl}-1,1,1-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol

HRID 49365

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=1[CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[O:13][CH2:14][C:15]1[S:16][C:17](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[C:22]#[CH:23])=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[F:43][C:44]([F:52])([F:51])[C:45]([C:47]([F:50])([F:49])[F:48])=[O:46]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=1[CH2:29][O:30][Si:31]([C:34]([CH3:36])([CH3:35])[CH3:37])([CH3:32])[CH3:33])[O:13][CH2:14][C:15]1[S:16][C:17](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[C:22]#[C:23][C:45]([C:47]([F:50])([F:49])[F:48])([OH:46])[C:44]([F:52])([F:51])[F:43])=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

1.7 g (3 mmol) of 2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-5-((E)-1-ethyl-but-1-en-3-ynyl)thiophene are dissolved in 50 mL of THF and the mixture is cooled to −78° C. 1.3 mL (3.3 mmol) of 2.5 M butyllithium are then added. After stirring for 15 minutes at the same temperature, a gentle flow of hexafluoroacetone (gas) is introduced into the reaction medium. After reaction for 20 minutes at −78° C., the flow of gas is stopped and the reaction medium is treated in the usual manner. The residue obtained is purified by chromatography on silica gel. The desired product is obtained in the form of a yellow oil (1 g).

Workup

customAfter reaction for 20 minutes at −78° C.
additionthe reaction medium is treated in the usual manner
customThe residue obtained
customis purified by chromatography on silica gel

Sources & evidence

ORD record: ord-22abab40fc7b49eeb1a7d05376d358b9
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Linked notes

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