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

HRID 2260848ノート

反応式

HRID 2260848 の反応式
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]

参加物

7

反応物 5

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

生成物 1

HCID 150144562-Fluoro-2-methyl-1-tetralone収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0dfa93ee75a4bcaaf1bc74e069c32f3
出典データセット
uspto-grants-1995_12
特許番号
US05478964

反応ノート

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