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Diisopropylethylamine → Carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester

HRID 1727011
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HRID 1727011 반응식
[CH3:1][O:2][C:3](=[O:16])[O:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22]Cl.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22][O:15][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([O:4][C:3](=[O:16])[O:2][CH3:1])[CH:14]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 15640638Carbonic acid 4-hydroxy-naphthalen-2-yl ester methyl ester

생성물 1

HCID 69036509Carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester수율 75.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
2 °C

실험 절차

4.62 g (21.2 mmol) of carbonic acid 4-hydroxy-naphthalen-2-yl ester methyl ester [Journal of Agricultural and Food Chemistry (1994), 42(12), 2970-2] was dissolved in 150 ml of MeCl2, 4.95 ml=4.71 g (25.4 mmol) of 2-(trimethylsilyl)-ethoxymethylchloride was added and this mixture cooled down to 2° C. 11.1 ml=8.38 g (63.5 mmol) of N-ethyl-diisoproylamine was added drop by drop and then, reaction was warmed up to ambient temperature. After 48 hours, it was poured into crashed ice and extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2) to give 5.57 g of carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester as colorless oil.

후처리

  1. customreaction
  2. temperaturewas warmed up to ambient temperature
  3. additionit was poured
  4. extractionextracted twice with MeCl2
  5. washthe organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2)

출처 및 근거

ORD 기록
ord-7f2463cb43b14d6b96528473969ee07e
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495001B2

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