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Chlorotriethylsilane → 1-benzyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde

HRID 1724023
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HRID 1724023 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:27]=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[Si:40](Cl)([CH2:45][CH3:46])([CH2:43][CH3:44])[CH2:41][CH3:42].[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:26][Si:40]([CH2:45][CH3:46])([CH2:43][CH3:44])[CH2:41][CH3:42])([C:22]([F:25])([F:23])[F:24])[C:18]([F:19])([F:20])[F:21])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:27]=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 13819ChlorotriethylsilaneHCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 115458181-benzyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde

생성물 1

HCID 210821981-benzyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde수율 92%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 0.33 g (0.82 mmol) of 1-benzyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde (example 23) in 3 mL of DMF at 0° C. were added 0.15 mL (0.99 mmol) of DBU, followed by 0.17 mL (0.99 mmol) of TESCl. The mixture was stirred at RT overnight and then poured into a mixture 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 0.389 g (92%) of 1-benzyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde, MS: 516 (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-7d8b8123ee004f5a8823283c2a2524ff
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07485652B2

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