Methyl trifluoromethyl ketone → 1-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne

HRID 35885

반응식

HRID 35885 반응식
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[CH:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[F:23][C:24]([F:29])([F:28])[C:25]([CH3:27])=[O:26]>O1CCCC1>[F:23][C:24]([F:29])([F:28])[C:25]([OH:26])([CH3:27])[C:17]#[C:16][C:13]1[CH:12]=[CH:11][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 9871Methyl trifluoromethyl ketoneHCID 199393204-PhenylsulfonylphenylethyneHCID 178418339Butyllithium

생성물 1

HCID 199393031-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne수율 75.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled (-78° C.) solution of 4-phenylsulfonylphenylethyne (66 mg, 0.27 mmol) in freshly distilled tetrahydrofuran (2.5 mL) was added n-BuLi (109 mL, 2.5M solution in hexanes, 0.27 mmol). The solution was stirred for 10 minutes at -78° C. at which time 1,1,1-trifluoroacetone (272 mL, 1.0M solution in tetrahydrofuran, 0.27 mmol) was added. The reaction mixture was kept at -78° C. for five minutes before quenching with 2N HCl . Diethyl ether was added, and the aqueous layer extracted further with diethyl ether. The combined organic layers were dried, evaporated and the product purified by chromatography, with ethyl acetate:hexanes as eluent (1:4) to yield the title butyne as a white solid (72 mg, 75%); mp 94.8°-95.3° C.; 250 MHz NMR (CDCl3): 1.72 (s,3, CH3), 3.08 (s,1, OH), 7.48-7.60 (m,5, Ar), 7.87-7.94 (m,4, Ar); MS: m/z=355(M+ 1). Analysis for C17H13F3O3S: Calculated: C, 57.62; H, 3.70; Found: C, 57.46; H, 3.65.

후처리

  1. additionwas added
  2. custombefore quenching with 2N HCl
  3. additionDiethyl ether was added
  4. extractionthe aqueous layer extracted further with diethyl ether
  5. customThe combined organic layers were dried
  6. customevaporated
  7. customthe product purified by chromatography, with ethyl acetate

출처 및 근거

ORD 기록
ord-15e03f81b99f4241a3b39f8284c311e9
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411973

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