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Potassium Phosphate, Tribasic → HCID 21981110, 화합물

HRID 10643
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HRID 10643 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1OS(C(F)(F)F)(=O)=O)=[O:2].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O.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>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[C:4]([C:20]2[S:19][CH:23]=[CH:22][CH:21]=2)[CH:5]=1
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참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27339602-Thiopheneboronic acidHCID 10802961HCID 10802961, 화합물

생성물 1

HCID 21981110HCID 21981110, 화합물수율 90%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매
HCID 962
Water
용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

Ex-34B: A solution of trifluoro-methanesulfonic acid 2-formyl-5-methoxy-phenyl ester (Ex-34A, 1.6 g, 5.63 mmol) in 1,4-dioxane (15 mL) was stirred at room temperature under nitrogen for 5 min. Thiophene-2-boronic acid (1.08 g, 8.44 mmol), tetrakis(triphenylphosphine)palladium(0) (0.65 g, 0.56 mmol) and a potassium phosphate (2.2 g, 10.36 mmol) were then added and the resulting mixture was heated to 95° C. under nitrogen overnight. Upon cooling to room temperature the reaction was diluted with EtOAc (25 mL) and water (25 mL) and the layers were cut. The organic phase was concentrated under reduced pressure. Silica gel chromatography (hexane/ethyl acetate, 4:1) gave 1.1 g (90%) of the desired 4-methoxy-2-thiophen-2-yl-benzaldehyde product. 1H-NMR (300 MHz, CDCl3): 10.06 (s, 1H), 8.03 (m, 1H), 7.45 (m, 1H), 7.14 (m, 1H), 7.09 (m, 1H), 7.00 (m, 2H), 3.91 (s, 3H).

후처리

  1. temperatureUpon cooling to room temperature the reaction
  2. concentrationThe organic phase was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8369248867f0408eb05df10e2fc0ea3b
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07094801B2

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