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

HRID 2371475노트

반응식

HRID 2371475 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7d36698dba284a6eb933148c69d96a2d
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05093356

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