Triethylamine → 2-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene

HRID 1367447

反応式

HRID 1367447 の反応式
BrC1[S:18][C:5]2[C:6]3[S:14][C:13]4[C:12]5[S:15][CH:16]=[CH:17][C:11]=5[S:10][C:9]=4[C:7]=3[S:8][C:4]=2[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[CH:29]#[C:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[CH2:39](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>[C:30]([C:29]1[S:18][C:5]2[C:6]3[S:14][C:13]4[C:12]5[S:15][CH:16]=[CH:17][C:11]=5[S:10][C:9]=4[C:7]=3[S:8][C:4]=2[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 129971-DecyneHCID 669248622-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene

生成物 1

HCID 669248432-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene収率 90.2%

試薬・触媒・溶媒 2

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

反応条件

温度
130 °C

実験手順

2-Bromo-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene (2.16 g, 4.6 mmol) (106) was mixed with 1-decyne (1.27 g, 9.2 mmolmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture was bubbled with nitrogen for 5 minutes and then heated up to 130° C. under argon for 16 hours. The triethylamine was evaporated and hexane (150 mL) was added. This mixture was filtered to remove solid salts. The organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3 g, 90.2%). 1HNMR: Solvent CD2Cl2. δ 7.41 (d, 1H), 7.33 (d, 1H), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m, 6H).

後処理

  1. customThis mixture was bubbled with nitrogen for 5 minutes
  2. customThe triethylamine was evaporated
  3. additionhexane (150 mL) was added
  4. filtrationThis mixture was filtered
  5. customto remove solid salts
  6. washThe organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL)
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by chromatography on silica gel
  10. washeluted with hexane

出典と根拠

ORDレコード
ord-a265aed53b1c4fe3a58e0958294b9f59
出典データセット
uspto-grants-2011_02
特許番号
US07893191B2

関連ノート

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