Toluene → (Z)-5-Fluoro-3-(2-hydroxyethyl)-2-methyl-1-(4-methylsulfonylbenzylidene)indene

HRID 379631노트

반응식

HRID 379631 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]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)/[C:6]([CH3:22])=[C:5]2[CH2:23][C:24](OC)=[O:25].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1COCC1>[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]([CH3:21])(=[O:19])=[O:20])=[CH:14][CH:13]=1)/[C:6]([CH3:22])=[C:5]2[CH2:23][CH2:24][OH:25]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 9952140Sulindac sulfone methyl esterHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 15860332(Z)-5-Fluoro-3-(2-hydroxyethyl)-2-methyl-1-(4-methylsulfonylbenzylidene)indene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of the ester from Step 1 (2.7 g, 7 mmol) in THF (20 mL) at 0° C. there was added diisobutyl aluminum hydride (1M) in toluene (17 mL, 17 mmol) and the mixture was stirred at 0° C. for 1 hour, then quenched with methanol (10 mL). Ethyl acetate and 1N aqueous HCl were added and after collection of the organic phase the aqueous phase was extracted once more with ethyl acetate. The combined organic extracts, after washing with water three times and drying over Na2SO4, afforded on evaporation a yellow residue which was triturated with ether to afford the title compound as a yellow solid, mp: 102-104° C.

후처리

  1. customquenched with methanol (10 mL)
  2. additionEthyl acetate and 1N aqueous HCl were added
  3. customafter collection of the organic phase the aqueous phase
  4. extractionwas extracted once more with ethyl acetate
  5. washThe combined organic extracts, after washing with water three times
  6. dry with materialdrying over Na2SO4
  7. customafforded on evaporation a yellow residue which
  8. customwas triturated with ether

출처 및 근거

ORD 기록
ord-aeb91c6641c6483bb8a0dd6b4ace3fbb
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300346B1

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