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

HRID 379640

반응식

HRID 379640 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e463c8082fe4fbbbdd06b9eff4ef69d
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300346B1

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