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Potassium Carbonate → (Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl ester

HRID 479209
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HRID 479209 반응식
[Cl-].[CH2:2]([O:4][CH:5]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:36]([O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=O)=[C:46]([CH3:52])[CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)(C)C>[CH2:9]([O:8][C:6](=[O:7])/[C:5](/[O:4][CH2:2][CH3:3])=[CH:48]/[C:47]1[CH:50]=[CH:51][C:44]([O:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:45][C:46]=1[CH3:52])[CH3:10]
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참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 27598062-Methyl 4-benzyloxybenzaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)3회

생성물 1

HCID 68617018(Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl ester수율 60%

시약·촉매·용매 1

HCID 3776Isopropanol
용매

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온도
60 °C

실험 절차

(Ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (3.79 g, 8.8 mmol) and potassium carbonate (1.46 g, 10.6 mmol) were added to a solution of 4-benzyloxy-2-methyl-benzaldehyde (0.8 g, 3.5 mmol) in isopropanol (10 ml) at 10° C. under an argon atmosphere [for the preparation of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride see: K. K. Bach, H. R. El-Seedi, H. M. Jensen, H. B. Nielsen, I. Thomson, K. B. G. Torssell, Tetrahedron 1994, 50, 7543-7556]. The suspension was heated to 60° C. After 12 h and after 20 h (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (each time 3.79 g, 8.8 mmol) and potassium carbonate (each time 1.46 g, 10.6 mmol) were added again. After 36 h the suspension was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with saturated aqueous ammonium chloride and ice water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, dichloromethane) to give 0.7 g (2.1 mmol, 58%) of the title compound as yellow liquid.

후처리

  1. filtrationAfter 36 h the suspension was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated aqueous ammonium chloride and ice water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography (silica gel, dichloromethane)

출처 및 근거

ORD 기록
ord-97199bd2b93641ba9ba3bddf38e9bdee
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06642389B2

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