Water → 2-Acetyl-4-(2-propoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene

HRID 1394601노트

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HRID 1394601 반응식
[CH:1]([C:4]1[C:5]([O:16][CH2:17][CH2:18][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[S:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:31](I)[C:25]=2[CH:24]=1)(=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.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>[C:20]([C:23]1[S:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:31]([C:6]3[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=3[O:16][CH2:17][CH2:18][CH3:19])[C:25]=2[CH:24]=1)(=[O:22])[CH3:21]

참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 121440122-Propoxy-3,5-diisopropyl-phenylboronic acidHCID 179527062-Acetyl-4-iodo benzo[b]thiophene

생성물 1

HCID 179527092-Acetyl-4-(2-propoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

A mixture of 1.08 mmol of 3,5-di-iso-propyl-2-propoxy phenylboronic acid, 1.62 mmol of 2-acetyl-4-iodo benzo[b]thiophene (see Example 14, step A) and 62 mg (0.05 mmol) of Pd(PPh3)4, 1 mL of 2N aqueous sodium carbonate in 9 mL of toluene and 4 mL ethanol was heated to reflux. After complexion (TLC), water was added and the solution was extracted with ethyl acetate. The organic layer is dried over MgSO4 and after evaporation of the solvents, the crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane) to afford 2-acetyl-4-(2-propoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene.

후처리

  1. temperaturewas heated to reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over MgSO4
  4. customafter evaporation of the solvents
  5. customthe crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-4a23e8a2ea7c4bc195e3f714c7e8f86a
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348359B2

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