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Dichloromethane → ethyl 8-(phenylethynyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854907
ノート
印刷プレビュー

反応式

HRID 854907 の反応式
I[C:2]1[CH:3]=[C:4]([O:21][C:22]([F:25])([F:24])[F:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.[C:26]1([C:32]#[CH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(Cl)Cl>C1(C)C=CC=CC=1.[Cl-].[Na+].O.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:26]1([C:32]#[C:33][C:2]2[CH:3]=[C:4]([O:21][C:22]([F:23])([F:25])[F:24])[CH:5]=[C:6]3[C:11]=2[O:10][CH:9]([C:12]([F:14])([F:15])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 6344DichloromethaneHCID 10821PhenylacetyleneHCID 86599457ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

生成物 1

HCID 86599458ethyl 8-(phenylethynyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate収率 85%

試薬・触媒・溶媒 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 1140Toluene溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (1.00 g, 2.07 mmole), phenylacetylene (0.455 mL, 4.15 mmole), CuI (39.5 mg, 0.207 mmole), PdCl2(dppf)2.CH2Cl2 (169 mg, 0.207 mmole) and TEA (0.867 mL, 6.22 mmole) in anhydrous toluene (10 mL) was stirred at room temperature for 18.5 h. The mixture was then poured into brine (100 mL) and extracted with EtOAc. The EtOAc layer was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica chromatography (9:1 hexanes:EtOAc) to give 0.802 g (85% yield) of the product as a yellow crystalline solid: EIHRMS m/z 456.0781 (M+, C14H14F6O4, Calc'd 456.0796).

後処理

  1. extractionextracted with EtOAc
  2. customThe EtOAc layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica chromatography (9:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-010d82e958fa4bfb919543624bb4f706
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259266B2

反応ノート

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