1-(Chloromethyl)-4-(methylthio)benzene → 2-Methyl-3-(4-methylthiobenzyl)-1-indanone

HRID 2371496

反応式

HRID 2371496 の反応式
[Li+].CC([N-]C(C)C)C.[CH3:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:19].[CH3:20][S:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>C1COCC1>[CH3:9][CH:10]1[CH:18]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([S:21][CH3:20])=[CH:23][CH:24]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:19]

参加物

5

反応物 3

HCID 701281-(Chloromethyl)-4-(methylthio)benzeneHCID 2492622-MethylindanoneHCID 2724682Lithium diisopropylamide

生成物 1

HCID 183674562-Methyl-3-(4-methylthiobenzyl)-1-indanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a cooled solution (-70° C.) of LDA (1M) in THF (37 mL) was added dropwise a solution of 2-methyl-1-indanone (J.A.C.S. Vol. 98, 8119-8124 (1976)) (2.5 g, 17 mmol) in THF (20 mL). The resulting dark red solution was stirred at room temperature for 3 hours, then cooled to -20° C. and a solution of 4-methylthiobenzyl chloride (3.1 g, 18 mmol) in THF (15 mL) was added slowly. The addition completed, the reaction mixture was stirred at -20° C. for 30 minutes before being quenched with 3N aqueous HCl (50 mL) and brine (50 mL). The product was extracted with ether, dried over MgSO4 and evaporated to dryness. The oily residue was chromatographed on silica gel eluting with a 1:5 mixture of ethyl acetate-hexane to afford the pure title compound as an oil.

後処理

  1. temperaturecooled to -20° C.
  2. additionThe addition
  3. stirringthe reaction mixture was stirred at -20° C. for 30 minutes
  4. custombefore being quenched with 3N aqueous HCl (50 mL) and brine (50 mL)
  5. extractionThe product was extracted with ether
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe oily residue was chromatographed on silica gel eluting with a 1:5 mixture of ethyl acetate-hexane

出典と根拠

ORDレコード
ord-8321a23e91b6492597d8c910d49f668f
出典データセット
uspto-grants-1992_03
特許番号
US05093356

関連ノート

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