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Phenyl isocyanate → 3-(1-Decyl)-5-isoxazolemethanol

HRID 235169
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HRID 235169 반응식
[N+:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([O-:3])=O.C[Si](C)(C)[O:17][C:18]#[C:19][CH3:20].C1(N=C=O)C=CC=CC=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:5]([C:4]1[CH:20]=[C:19]([CH2:18][OH:17])[O:3][N:1]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
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참가 물질

6

반응물 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 109873051-NitroundecaneHCID 13614841O-trimethylsilylpropynol

생성물 1

HCID 183729453-(1-Decyl)-5-isoxazolemethanol수율 34.5%

시약·촉매·용매 1

HCID 241Benzene용매2회

반응 조건

온도
60 °C

실험 절차

To a solution of 1-nitroundecane (38.0 g) and O-trimethylsilylpropynol (24.1 g) in dry benzene (300 ml) was added dropwise a solution of freshly distilled phenylisocyanate (44.9 g) and triethylamine (22.4 g) in dry benzene (50 ml) at 40° C., with stirring. The reaction mixture was heated at 60° C. for 3 hrs, cooled, and filtered. To the filtrate was added 1.0M tetrabutylammonium fluoride (40 ml). After 30 mins, the solution was evaporated, and the residue was flash chromatographed (silica gel, 1% methanol-dichloromethane) to give 15.5 g (34%) of product, mp 55°-56° C.

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. additionTo the filtrate was added 1.0M tetrabutylammonium fluoride (40 ml)
  4. customthe solution was evaporated
  5. customchromatographed (silica gel, 1% methanol-dichloromethane)

출처 및 근거

ORD 기록
ord-db5fd9ecac524d4c942b93abfc140b20
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05597838

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