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Sodium Carbonate → Ethyl 2-[4-(5-chlorothiophen-2-yl)-phenoxy]-4-cyclohex-1-enylbutanoate

HRID 1867462
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HRID 1867462 반응식
[Cl:1][C:2]1[S:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH2:24][CH2:25][C:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[Cl:1][C:2]1[S:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH2:24][CH2:25][C:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=3)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27343245-Chlorothiophene-2-boronic acidHCID 66999225Ethyl 2-[(4-bromophenyl)oxy]-4-cyclohex-1-en-1-ylbutanoate

생성물 1

HCID 66999601Ethyl 2-[4-(5-chlorothiophen-2-yl)-phenoxy]-4-cyclohex-1-enylbutanoate수율 73%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

0.18 g (0.04 equivalent) of Pd(PPh3)4 and then 1.2 g (0.0084 mol) of 5-chloro-2-thiopheneboronic acid are added to a solution of 1.4 g (0.0038 mol) of ethyl 2-[(4-bromophenyl)oxy]-4-cyclohex-1-en-1-ylbutanoate in 20 ml of dimethoxyethane. 4.2 ml of 2M sodium carbonate solution are added at room temperature. The reaction mixture is stirred overnight and then refluxed for 2 hours. After cooling to room temperature, the mixture is taken up in water and extracted with ethyl acetate. The extract is washed with 1N sodium hydroxide and then with saturated aqueous NaCl solution and finally dried over Na2SO4. After concentrating, the black oil obtained is purified by flash chromatography (95/5 heptane/ethyl acetate). 1.1 g of a thick oil are obtained.

후처리

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with 1N sodium hydroxide
  4. dry with materialwith saturated aqueous NaCl solution and finally dried over Na2SO4
  5. concentrationAfter concentrating
  6. customthe black oil obtained
  7. customis purified by flash chromatography (95/5 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-710eb2a53d794e2dbf76930e61c80772
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07632846B2

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