HCID 67054652, compound → HCID 67054654, compound

HRID 868788Notes

Reaction equation

HRID 868788 reaction equation
[CH2:1]([CH:3]([CH2:49][CH2:50][CH2:51][CH3:52])[C:4]#[C:5][C:6]1[C:24]2[S:25][C:26]([Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])=[CH:27][C:23]=2[C:22]([C:38]#[C:39][CH:40]([CH2:47][CH3:48])[CH2:41][CH2:42][CH2:43][CH2:44]CC)=[C:8]2[S:9][C:10]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[CH:11][C:7]=12)[CH3:2]>[Pd]>[CH2:47]([CH:40]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:39][CH2:38][C:22]1[C:8]2[S:9][C:10]([Si:12]([CH:16]([CH3:18])[CH3:17])([CH:19]([CH3:20])[CH3:21])[CH:13]([CH3:15])[CH3:14])=[CH:11][C:7]=2[C:6]([CH2:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:49][CH2:50][CH2:51][CH3:52])=[C:24]2[S:25][C:26]([Si:28]([CH:35]([CH3:36])[CH3:37])([CH:32]([CH3:33])[CH3:34])[CH:29]([CH3:30])[CH3:31])=[CH:27][C:23]=12)[CH3:48]

Participants

3

Reactant 1

HCID 67054652HCID 67054652, compound

Product 1

HCID 67054654HCID 67054654, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
95 °C

Procedure

A dry 100 mL three-neck round bottom flask equipped with a condenser was flushed with N2 and was charged with (4-(3-ethylhept-1-yn-1-yl)-8-(3-ethylnon-1-yn-1-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(triisopropylsilane) (2.5 g, 3.3 mmol), Pd/C dry support (0.70 g, 10%) and anhydrous 1,4-dioxane (30 mL, 0.11 M). The flask was evacuated and backfilled with hydrogen. The reaction was kept under a hydrogen atmosphere and slowly heated to 95° C. Completion of hydrogenation was monitored by TLC. After hydrogenation was complete, the mixture was cooled to ambient temperature, filtered through Celite, and solvent was removed by rotary evaporation. The solid was dissolved in chloroform and precipitated into methanol to yield white solid (2.42 g, 97%).

Workup

  1. customA dry 100 mL three-neck round bottom flask equipped with a condenser
  2. customwas flushed with N2
  3. dry with materialdry support (0.70 g, 10%) and anhydrous 1,4-dioxane (30 mL, 0.11 M)
  4. customThe flask was evacuated
  5. temperaturethe mixture was cooled to ambient temperature
  6. filtrationfiltered through Celite, and solvent
  7. customwas removed by rotary evaporation
  8. dissolutionThe solid was dissolved in chloroform
  9. customprecipitated into methanol

Sources & evidence

ORD record
ord-f275511029c2451f829e41ad681bcf62
Source dataset
uspto-grants-2015_03
Patent number
US08968885B2

Reaction notes

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