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Lithium hexamethyldisilazane → 4-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid

HRID 2395074
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HRID 2395074 반응식
[Br-].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1)([OH:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:42]([O:49][C:50]1[C:51]([CH:56]=O)=[N:52][CH:53]=[CH:54][CH:55]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1COCC1>[CH2:42]([O:49][C:50]1[C:51]([CH:56]=[CH:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:2]([OH:4])=[O:3])=[CH:10][CH:9]=2)=[N:52][CH:53]=[CH:54][CH:55]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 2733832Lithium hexamethyldisilazaneHCID 133745943-(Benzyloxy)pyridine-2-carbaldehydeHCID 226755274-Carboxyphenethyltriphenylphosphonium bromide

생성물 1

HCID 544494594-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

(2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (0.58 g, 1.17 mmol) was suspended in THF (7 ml) and lithium bis(trimethylsilyl)amide was added (1M in THF, 2.46 ml). The reaction mixture turned orange and was allowed to stir for 1 hour at ambient temperature. A solution of 3-benzyloxy-2-pyridinecarbaldehyde (0.25 g, 1.17 mmol) in THF (3.5 ml) was added slowly. The reaction was stirred at ambient temperature for 1 hour. The reaction was quenched by the addition of water (8 ml) and ether (8 ml). The layers were separated, the ether layer was washed with water and the as aqueous layers were combined, acidified with 1N HCl and extracted with EtOAc (2×). The organic extracts were dried (MgSO4) and evaporated to give the title product as a mixture of isomers (2.7 g 66%).

후처리

  1. stirringThe reaction was stirred at ambient temperature for 1 hour
  2. customThe reaction was quenched by the addition of water (8 ml) and ether (8 ml)
  3. customThe layers were separated
  4. washthe ether layer was washed with water
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-6441c0bbfdf043f2804789475f0dcf23
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05811459

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