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

反応式

[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]

参加物

反応条件

温度: -78 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-22abab40fc7b49eeb1a7d05376d358b9
出典データセット: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06706725B1

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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