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

HRID 1420732ノート

反応式

HRID 1420732 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]([CH3:21])(=[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]

参加物

5

反応物 3

HCID 1140TolueneHCID 9952140Sulindac sulfone methyl esterHCID 21225700Diisobutylaluminumhydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de24a7805db34dcfa0c45dfec1affe15
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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