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Hydrochloric Acid → {2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester

HRID 852365
ノート
印刷プレビュー

反応式

HRID 852365 の反応式
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]#[CH:18])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2].I[C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1.CCN(CC)CC.Cl>CN(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.[Cu]I.CCOCC>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]#[C:18][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 86602538(2-Methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester

生成物 1

HCID 69458063{2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester収率 52.8%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A degassed (argon) solution of 96.0 mg (0.33 mmol) (2-methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester, 0.053 ml (0.36 mmol) 1-iodo-4-trifluoromethyl-benzene and 0.086 (0.621 mmol) Et3N in 1 ml DMF was treated with 37.9 mg (0.03 mmol) Pd(PPh3)4 and 12.5 mg (0.07 mmol) of CuI. After stirring for 2 h at room temperature, the reaction was distributed between 1N HCl and ether (three times). Washing of the organic layer with saturated aqueous NH4Cl solution and brine, drying (Na2SO4) and evaporation of the solvents, followed by flash chromatography (SiO2, n-heptane/EtOAc 1 to 5%), yielded 76 mg of the title compound as yellow oil.

後処理

  1. washWashing of the organic layer with saturated aqueous NH4Cl solution and brine
  2. customdrying
  3. custom(Na2SO4) and evaporation of the solvents

出典と根拠

ORDレコード
ord-b304c27d0097490cb727dbc9e1390786
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07253192B2

反応ノート

読み込み中…

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