Hydrochloric Acid → (Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetaldehyde

HRID 1420721ノート

反応式

HRID 1420721 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22](OC)=[O:23].[H-].C([Al+]CC(C)C)C(C)C.CO.Cl>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH:22]=[O:23]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 16046334Sulindac Sulfide Methyl EsterHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 86745520(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
-70 °C

実験手順

To a solution of the ester from Step 1 (3.39 g, 9.57 mmol) in toluene (75 mL) at -70° C., there was slowly added diisobutyl aluminum hydride (1M) in toluene (12 mL, 12 mmol) and the resulting mixture stirred at -70° C. for 45 minutes. Methanol (10 mL) was added slowly at -70° C., then the mixture was warmed to room temperature and water (100 mL) and 1N aqueous HCl (50 mL) were added. The mixture was shaken and the organic layer collected; the aqueous fraction was extracted with ether and the combined organic fractions washed 3 times with water, dried over MgSO4 and evaporated down to a thick oil. The crude title compound was used as such in the next step.

後処理

  1. customat -70° C.
  2. temperaturethe mixture was warmed to room temperature
  3. stirringThe mixture was shaken
  4. customthe organic layer collected
  5. extractionthe aqueous fraction was extracted with ether
  6. washthe combined organic fractions washed 3 times with water
  7. dry with materialdried over MgSO4
  8. customevaporated down to a thick oil

出典と根拠

ORDレコード
ord-c7c4da16d7aa4f4c8e7bf7a64d7cadd6
出典データセット
uspto-grants-2000_06
特許番号
US06071934

反応ノート

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