Potassium Hydroxide → 2-Carboxy-2-(4-methoxybenzylthio)indan

HRID 260683ノート

反応式

HRID 260683 の反応式
[C:1]([C:5]1([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([O:3]C)=[O:2].[OH-].[K+]>C(O)C.O.O1CCCC1>[C:1]([C:5]1([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)([OH:3])=[O:2]

参加物

6

反応物 2

HCID 14797Potassium HydroxideHCID 152807342-(Carbomethoxy)-2-(4-methoxybenzylthio)indan

生成物 1

HCID 152807352-Carboxy-2-(4-methoxybenzylthio)indan収率 43%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indan (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 hexane/ethylacetate) to give 2-carboxy-2-(4-methoxybenzylthio)indan as a yellow solid (0.48 g).

後処理

  1. filtrationFilter
  2. customevaporate the solvent in vacuo
  3. customPartition between water (125 mL) and ether (75 mL)
  4. customSeparate the aqueous phase
  5. extractionExtract with methylene chloride (75 mL)
  6. dry with materialdry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by silica gel chromatography (2:1 hexane/ethylacetate)

出典と根拠

ORDレコード
ord-257c792d28c74c88bfa09731d082fe5b
出典データセット
uspto-grants-1996_06
特許番号
US05529996

反応ノート

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