Triphenylphosphine → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-(2-hydroxyethoxyphenylethynyl)cyclohexan-1-one

HRID 442709

反応式

HRID 442709 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)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>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][CH2:26][CH2:25][OH:24])[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 105635432-Hydroxyethoxy-1-iodobenzeneHCID 153920073-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

生成物 1

HCID 218309293-(3-Cyclopentyloxy-4-methoxyphenyl)-3-(2-hydroxyethoxyphenylethynyl)cyclohexan-1-one収率 14%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

To a solution of the compound from Example 3 (E1) (0.25 g, 0.8 mmol) and 2-hydroxyethoxy-1-iodobenzene (0.21 g, 0.8 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 1 h, was cooled to room temperature and was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, was dried (MgSO4) and was evaporated. Purification by flash chromatography, eluting with 1:1 hexanes/ethyl acetate, provided the tide compound as a white solid (0.05 g, 14%), m.p. 93°-94° C.

後処理

  1. temperaturewas cooled to room temperature
  2. concentrationwas concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried (MgSO4)
  6. customwas evaporated
  7. customPurification by flash chromatography
  8. washeluting with 1:1 hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-eb1182658d0447b79dc97b1f066b85fc
出典データセット
uspto-grants-1999_04
特許番号
US05891883

関連ノート

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