Diisopropylamine → 2-Fluoro-2-methyl-1-tetralone

HRID 1656808노트

반응식

HRID 1656808 반응식
C(NC(C)C)(C)C.C([Li])CCC.C(NC(C)C)(C)C.[Li].[CH3:21][CH:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:43])(=O)=O)=CC=1>O1CCCC1>[CH3:21][C:22]1([F:43])[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32]

참가 물질

7

반응물 5

HCID 7912DiisopropylamineHCID 1026502-Methyl-1-tetraloneHCID 588007N-FluorobenzenesulfonimideHCID 45051747Lithium diisopropylamineHCID 178418339Butyllithium

생성물 1

HCID 150144562-Fluoro-2-methyl-1-tetralone수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

0.16 milliliter diisopropylamine in 10 milliliters tetrahydrofuran were allowed to stand with 1.15 equivalents butyllithium at -25° C. The resulting solution of lithium diisopropylamine was cooled to -78° C. and 1 equivalent 2-methyl-1-tetralone in 5 milliliters tetrahydrofuran solution was dropped in. The mixture was allowed to stand at -70° C. for 100 minutes. 1.5 equivalents N-fluorobenzenesulfonimide prepared according to Example 1 above in 11 milliliters tetrahydrofuran were mixed rapidly with the mixture at -95° C. The mixture was quenched with 30 milliliters ammonium chloride solution and extracted with dichloromethane. The organic phase was dried with magnesium sulfate, filtered, and evaporated. 2-methyl-2-fluoro-tetralone was obtained in 50% yield.

후처리

  1. additionwere mixed rapidly with the mixture at -95° C
  2. customThe mixture was quenched with 30 milliliters ammonium chloride solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-225051308dab4752838f27b03d9e6062
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254732

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