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

반응식

HRID 49365 반응식
[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]

참가 물질

5

반응물 3

HCID 12695HexafluoroacetoneHCID 880121392-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-5-((E)-1-ethyl-but-1-en-3-ynyl)thiopheneHCID 178418339Butyllithium

생성물 1

HCID 20636349(e)-6-{5-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-2-thienyl}-1,1,1-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-22abab40fc7b49eeb1a7d05376d358b9
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706725B1

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