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

HRID 1867462
ノート
印刷プレビュー

反応式

HRID 1867462 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-710eb2a53d794e2dbf76930e61c80772
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632846B2

反応ノート

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