Acetic Acid → Benzyl 4-hydroxy-1H-indole-1-carboxylate

HRID 16569

반응식

HRID 16569 반응식
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 11703628Benzyl 4-(t-butyldimethylsilyloxy)indole-1-carboxylate

생성물 1

HCID 12622101Benzyl 4-hydroxy-1H-indole-1-carboxylate수율 70.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of 10 (28.62 g, 75 mmol) in tetrahydrofuran (375 mL) containing acetic acid (4.5 g, 75 mmol) was treated at 0° C. with 1 M tetrabutylammonium fluoride (75 mL, 75 mmol) and the mixture was stirred at 0° C. for 40 min. The solvent was evaporated and the residue was dissolved in diethyl ether (250 mL) and washed with saturated aq. sodium bicarbonate and brine, dried and evaporated to give a brown solid which was washed with cold hexanes to give 11 as white fluffy needles (14.13 g, 70%), mp 118-120° C. (from dichloromethane-hexanes), (lit.11 mp 121-124° C.).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in diethyl ether (250 mL)
  3. washwashed with saturated aq. sodium bicarbonate and brine
  4. customdried
  5. customevaporated
  6. customto give a brown solid which
  7. washwas washed with cold hexanes

출처 및 근거

ORD 기록
ord-7b6517d98c05498aa1c66ec4e8f2faff
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737169B2

연결된 노트

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