Tetrahydrofuran → HCID 66870587, compound

HRID 1691582Notes

Reaction equation

HRID 1691582 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:7]([Mg]Cl)([CH3:9])[CH3:8].[S:12]1[CH:16]=[CH:15][C:14]2[C:17](=O)[C:18]3[S:19][CH:20]=[CH:21][C:22]=3C(=O)[C:13]1=2.Cl[Sn]Cl.[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>Cl>[C:7]([C:9]1[C:13]2[S:12][CH:16]=[CH:15][C:14]=2[C:17]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])=[C:18]2[S:19][CH:20]=[CH:21][C:22]=12)#[C:8][CH2:33][CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 127321-HexyneHCID 24479Stannous ChlorideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 178418918HCID 178418918, compound

Product 1

HCID 66870587HCID 66870587, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of hexyne (6.71 grams, 81.7 mmol) in THF (20 milliliters) in a 100 milliliter flask equipped with a condenser under an argon atmosphere were added dropwise 36 milliliters (72 mmol) of 2 M solution of isopropylmagnesium chloride in THF at room temperature. An exothermic reaction occurred upon addition. After addition, the reaction mixture was heated at 50° C. for 95 minutes and cooled down to room temperature. Benzo[1,2-b:4,5-b′]dithiophene-4,8-dione (3 grams, 13.6 mmol) was added, and the mixture was heated at 50° C. for 1 hour before cooling down to room temperature. Subsequently, a solution of 20 grams of SnCl2 in 50 milliliters 10 percent aq. HCl solution was added in a dropwise fashion followed by a further heating at 60° C. for 1 hour. After the reaction, the solvent was removed by vacuum evaporation, and the residue was purified by passing through a silica-gel flash column (eluent: hexane/dichloromethane, 2/1, v/v). Recrystallization of the crude product collected from flash chromatography from 2-propanol gave 3 grams (63 percent yield) of a red crystal after drying in vacuo.

Workup

  1. customAn exothermic reaction
  2. additionoccurred upon addition
  3. additionAfter addition
  4. temperaturecooled down to room temperature
  5. temperaturethe mixture was heated at 50° C. for 1 hour
  6. temperaturebefore cooling down to room temperature
  7. temperaturea further heating at 60° C. for 1 hour
  8. customAfter the reaction
  9. customthe solvent was removed by vacuum evaporation
  10. customthe residue was purified
  11. customRecrystallization of the crude product
  12. customcollected from flash chromatography from 2-propanol

Sources & evidence

ORD record
ord-a629b40d96d24a299856db799ff17714
Source dataset
uspto-grants-2012_04
Patent number
US08153755B2

Reaction notes

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