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Monobenzone → Methyl 3-(4-(2-[4-(benzyloxy)phenoxy]ethyl)phenyl)-2-chloropropanoate

HRID 33814
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인쇄 미리보기

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HRID 33814 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][CH:21]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][OH:35])=[CH:29][CH:28]=1)[C:22]([O:24][CH3:25])=[O:23].[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47]([O:35][CH2:34][CH2:33][C:30]2[CH:29]=[CH:28][C:27]([CH2:26][CH:21]([Cl:20])[C:22]([O:24][CH3:25])=[O:23])=[CH:32][CH:31]=2)=[CH:46][CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7638MonobenzoneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86600802Methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate

생성물 1

HCID 86600803Methyl 3-(4-(2-[4-(benzyloxy)phenoxy]ethyl)phenyl)-2-chloropropanoate수율 67.1%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
55 °C

실험 절차

Triphenylphosphine (2.4 g, 9 mmol) was added to a solution of methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate (2.1 g, 8.5 mmol) and 4-(benzyloxy)phenol (1.7 g, 8 mmol) in 20 ml toluene under nitrogen atmosphere. The solution was warmed to 55° C. and diisopropyl azodicarboxylate (1.8 g, 9 mmol) was added. The reaction mixture was stirred at 55° C. overnight. The mixture was allowed to cool and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography using a 80:20 mixture of heptane and EtOAc as eluent to yield 2.28 g of the desired product (yield 61%) as colourless crystals.

후처리

  1. temperatureto cool
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude product was purified by flash chromatography
  4. additiona 80:20 mixture of heptane and EtOAc as eluent

출처 및 근거

ORD 기록
ord-b1dbfc4476ed401d93f87254f4a51af6
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07429675B2

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