Triphenylphosphine → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-[3-(5-methyl-[1,3,4]thiadiazol-2-yl)phenylethynyl]cyclohexan-1-one

HRID 1600862ノート

反応式

HRID 1600862 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.I[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[S:32][C:33]([CH3:36])=[N:34][N:35]=2)[CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.[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:25][CH:26]=[C:27]([C:31]5[S:32][C:33]([CH3:36])=[N:34][N:35]=5)[CH:28]=4)[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

6

反応物 3

HCID 11776TriphenylphosphineHCID 153920073-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-oneHCID 193499822-(3-Iodophenyl)-5-methyl-1,3,4-thiadiazole

生成物 1

HCID 154341633-(3-Cyclopentyloxy-4-methoxyphenyl)-3-[3-(5-methyl-[1,3,4]thiadiazol-2-yl)phenylethynyl]cyclohexan-1-one収率 87%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8471Triethylamine溶媒

実験手順

To a solution of the compound from Example 3 (E1) (0.10 g, 0.32 mmol) and 1-iodo-3-(5-methyl-[1,3,4]thiadiazol-2-yl)benzene (0.10 g, 0.32 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palldium(0), copper(I) iodide and triphenylphosphine. The mixture was refluxed for 0.20 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 title compound as a white solid (0.135 g, 87%), m.p. 97-99° C.

後処理

  1. temperatureThe mixture was refluxed for 0.20 h
  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-33468fab21004c8fa9e4e6b0369ff52c
出典データセット
uspto-grants-1999_11
特許番号
US05977122

反応ノート

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