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

HRID 16569

反応式

HRID 16569 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 12622101Benzyl 4-hydroxy-1H-indole-1-carboxylate収率 70.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-7b6517d98c05498aa1c66ec4e8f2faff
出典データセット
uspto-grants-2010_06
特許番号
US07737169B2

関連ノート

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