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Ammonium Chloride → 1-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopropan-1-ol

HRID 1371270
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HRID 1371270 반응식
[Si:1]([O:18][CH2:19][C:20]([O:22]CC)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([Mg]Br)[CH3:26].[Cl-].[NH4+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Si:1]([O:18][CH2:19][C:20]1([OH:22])[CH2:26][CH2:25]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 59464758(tert-Butyl-diphenyl-silanyloxy)-acetic acid ethyl esterHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 529878051-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopropan-1-ol수율 100%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매
HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

According to the description in a reference (see: Syn. Lett. 07, 1053–1054, 1999), the title compound was prepared as follows. 12 g (35 mmole) of ethyl 2-{[t-butyl(diphenyl)silyl]oxy}acetate was dissolved in 200 ml of tetrahydrofuran (THF) and 2.2 ml of titaniumtetraisopropoxide was added thereto. To the mixture was slowly added 29.2 ml of ethylmagnesiumbromide (3.0M in THF), and the reaction solution was stirred for 12 hours at room temperature. 20 ml of saturated ammonium chloride was added to stop the reaction. About 150 ml of tetrahydrofuran (THF) used as a solvent was removed by distillation under reduced pressure, and the reaction mixture was extracted twice with 200 ml of ethyl acetate. The ethyl acetate extract was distilled under reduced pressure to give 11.4 g (Yield 100%) of the title compound as a white solid.

후처리

  1. customthe title compound was prepared
  2. customthe reaction
  3. customwas removed by distillation under reduced pressure
  4. extractionthe reaction mixture was extracted twice with 200 ml of ethyl acetate
  5. extractionThe ethyl acetate extract
  6. distillationwas distilled under reduced pressure

출처 및 근거

ORD 기록
ord-30b3a42e6e384fc8a0d30b8dc6ff8dba
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07157448B2

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