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

HRID 379641

反応式

HRID 379641 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3b1aab1c433143d5836a91946510fbde
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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