tert-butyl 3-formyl-1H-indole-1-carboxylate → tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 742550ノート

反応式

HRID 742550 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][OH:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 2764519tert-butyl 3-formyl-1H-indole-1-carboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 11075767tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a 100mL two-necked round-bottom flask equipped with a thermometer 1-(tert-butyloxycarbonyl)-3-formylindole (13.7 g, 60 mmol) was suspended in ethanol (36 mL). Sodium borohydride (4.40 g, 115 mmol) was added in four portions, during which the temperature did not rise about 20° C., and the mixture was stirred for 6 hours. Then the solvent was evaporated in vacuo. The residual oil was shaken with 1.0N sodium hydroxide (150 mL), and the alkaline solution was extracted with ether (3×180 mL), dried with MgSO4, filtered and evaporated to give a colorless oil which solidified on refrigeration (3.95 g, ca. 100%).

後処理

  1. customdid not rise about 20° C.
  2. customThen the solvent was evaporated in vacuo
  3. stirringThe residual oil was shaken with 1.0N sodium hydroxide (150 mL)
  4. extractionthe alkaline solution was extracted with ether (3×180 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a colorless oil which

出典と根拠

ORDレコード
ord-dfca2fed31e6457aad0fc6eb447d512a
出典データセット
uspto-grants-1996_09
特許番号
US05554753

反応ノート

読み込み中…