Diethyl Ether → (1-Benzyl-5-bromo-1H-indol-2-yl)methanol

HRID 346840노트

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HRID 346840 반응식
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].CCOCC>C1COCC1>[Br:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([CH2:4][OH:3])=[CH:14]2

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21964289Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

생성물 1

HCID 21964298(1-Benzyl-5-bromo-1H-indol-2-yl)methanol수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 6.7 g (19 mmol) of 5-bromo-1-(benzyl)indole-2-carboxylic acid ethyl ester in 25 mL of anhydrous THF at 0° C. were added portionwise 1.42 g (37 mmol) of LiAlH4 and the resulting mixture was stirred at 0° C. for 2 h. After addition of a saturated aqueous solution of NH4Cl and Et2O, the phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 5.8 g (ca 19 mmol) of [5-bromo-1-(benzyl)-1H-indol-2-yl]-methanol, that was dissolved in 30 mL of CH2Cl2 and treated at 0° C. with 4.75 mL (28 mmol) of DIPEA 7.5 mL (28 mmol) of TIPSOTf. The mixture was stirred at RT for 1 h and added to saturated aqueous NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 7.3 g (81%) of 5-bromo-1-(benzyl)-2-triisopropylsilanyloxymethyl-1H-indole, off-white solid, MS: 473 (MH+).

후처리

  1. customthe phases were separated
  2. extractionthe aqueous one was extracted with Et2O
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-227a897fc16942fba4042d558ebc8ef4
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173048B2

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