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

HRID 742550노트

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HRID 742550 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dfca2fed31e6457aad0fc6eb447d512a
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554753

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