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Hydrochloric Acid → 3-Chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

HRID 1453328
ノート
印刷プレビュー

反応式

HRID 1453328 の反応式
[CH2:1]([C:5]1([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[O:10][C:9](=[O:11])[CH:8]([Cl:12])[C:7](=[O:13])[CH2:6]1)[CH2:2][C:3]#[CH:4].I[C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.Cl>CN(C=O)C.C(NC(C)C)(C)C.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:12][CH:8]1[C:7](=[O:13])[CH2:6][C:5]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)([CH2:1][CH2:2][C:3]#[C:4][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[O:10][C:9]1=[O:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 3

HCID 313Hydrochloric AcidHCID 122723-IodophenolHCID 224997916-But-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione

生成物 1

HCID 587622273-Chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418476
HCID 178418476、化合物
触媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒
HCID 7912Diisopropylamine溶媒

反応条件

温度
90 °C

実験手順

A solution of 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione (200 mg, 0.66 mmol) from Step 4 above, 3-iodophenol (145 mg, 0.66 mmol), bis(triphenylphosphine)palladium (II) dichloride (18 mg, 0.026 mmol), and copper (I) iodide (10 mg, 0.052 mmol) in DMF (0.66 mL) and diisopropylamine (0.66 mL) was sonicated for 1 minute and then heated to 90° C. for 20 minutes. The reaction was cooled to room temperature, and then diluted with 10 mL CH2Cl2 The reaction was then neutralized to a pH of 4 with 6 N HCl and the layers were separated. The aqueous layer was extracted with 3×10 mL CH2Cl2 and the organic layers were combined, and then dried over sodium sulfate. After filtering the solids, the organic layer was concentrated to a dark oil, which was used without further purification. MS (ESI): 359 (M−H), 361 (M+2−H).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with 3×10 mL CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering the solids
  6. concentrationthe organic layer was concentrated to a dark oil, which
  7. customwas used without further purification

出典と根拠

ORDレコード
ord-6f83910178fe4c869d813fa15c162d47
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07473790B2

反応ノート

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