Sodium Carbonate → HCID 59682040、化合物

HRID 1394631ノート

反応式

HRID 1394631 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

HCID 59682040HCID 59682040、化合物収率 58.1%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a0c574dbc65b4572b48ccc6cbcbc502b
出典データセット
uspto-grants-2008_03
特許番号
US07348359B2

反応ノート

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