Sodium Carbonate → HCID 59682040, 화합물

HRID 1394631노트

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HRID 1394631 반응식
[CH:1]([C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:20]([C:23]1[CH:39]=[CH:38][C:26]2[S:27][CH:28]=[C:29](OS(C(F)(F)F)(=O)=O)[C:25]=2[CH:24]=1)(=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]([C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([C:29]2[C:25]3[CH:24]=[C:23]([C:20](=[O:22])[CH3:21])[CH:39]=[CH:38][C:26]=3[S:27][CH:28]=2)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 10999969HCID 10999969, 화합물HCID 59682035Trifluoro-methanesulfonic acid 5-acetyl-benzo[b]thiophen-3-yl ester

생성물 1

HCID 59682040HCID 59682040, 화합물수율 58.1%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

실험 절차

3,5-Diisopropyl-2-methoxymethoxy-phenyl-boronic acid (470 mg, 1.8 mmol) was dissolved in toluene (15 ml) and ethanol (15 ml). Trifluoro-methanesulfonic acid 5-acetyl-benzo[b]thiophen-3-yl ester (320 mg, 0.99 mmol), tetrakis(triphenylphosphine)palladium(0) (114 mg, 0.1 mmol) followed by some 2M sodium carbonate solution (1.98 mmol) was added to this solution. The reaction was then heated overnight, then poured into brine (20 ml) and extracted with ethyl acetate (2×20 ml). The organic layers were then dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (chromatotron, 4μ plate, 0-10% ethyl acetate in hexanes) to give 1-[3-(3,5-diisopropyl-2-methoxymethoxy-phenyl)-benzo[b]thiophen-5-yl]-ethanone as a yellow oil (228 mg, 58%). An analytical sample was obtained by preparatory thin layer chromatography (5% ethyl acetate in hexanes). 1HNMR (250 MHz, CDCl3): δ 8.23 (s, 1H), 7.85-7.97 (m, 2H), 7.48 (s, 1H), 7.14 (d, 1H, J=1.2),7.04 (d, 1H, J=1.2),4.41 (s, 2H), 3.40 (m, 1H), 2.95 (s, 3H), 2.86 (m, 1H), 2.55 (s, 3H), 1.26 (s, 3H), 1.23 (s, 3H), 1.21, (s, 3H), 1.18 (s, 3H).

후처리

  1. additionwas added to this solution
  2. temperatureThe reaction was then heated overnight
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. dry with materialThe organic layers were then dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (chromatotron, 4μ plate, 0-10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-a0c574dbc65b4572b48ccc6cbcbc502b
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348359B2

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