Hydrochloric Acid → Methyl 2-methyl-3-(4-methylthiobenzyl)inden-1-ylacetate

HRID 379641

반응식

HRID 379641 반응식
[CH3:1][CH:2]1[CH:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].II.Cl>CCOCC.[Zn]>[CH3:1][C:2]1[CH:3]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 60984Methyl bromoacetateHCID 183674562-Methyl-3-(4-methylthiobenzyl)-1-indanone

생성물 1

HCID 18367447Methyl 2-methyl-3-(4-methylthiobenzyl)inden-1-ylacetate

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

To a solution of the indanone derivative from Step 1 (885 mg, 3.14 mmol) in ether (20 mL) were added successively zinc (840 mg, 12.8 mmol), methyl bromoacetate (0.5 mL, 5 mmol) and iodine (200 mg). The reaction mixture was refluxed for 3 hours, then cooled to 0° C. and 6N aqueous HCl was added dropwise until the zinc complex was completely decomposed. The organic layer was decanted, washed with brine, dried over Na2SO4 and evaporated to dryness. The oily residue was dissolved in formic acid and evaporated to dryness to complete the dehydration of the intermediate methyl [1-hydroxy-2-methyl-3-(4-methylthiobenzyl)indan-1-yl]acetate. The resulting oily residue was chromatographed on silica gel eluting with a 1:19 mixture of ethyl acetate-hexane to afford pure title compound as an oil.

후처리

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customThe organic layer was decanted
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. dissolutionThe oily residue was dissolved in formic acid
  7. customevaporated to dryness
  8. customThe resulting oily residue was chromatographed on silica gel eluting with a 1:19 mixture of ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-3b1aab1c433143d5836a91946510fbde
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300346B1

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