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

HRID 379640

反応式

HRID 379640 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 (1 M) 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 for 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-6e463c8082fe4fbbbdd06b9eff4ef69d
出典データセット
uspto-grants-2001_10
特許番号
US06300346B1

関連ノート

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