Carbon Dioxide → HCID 53682346, compound

HRID 1200050Notes

Reaction equation

HRID 1200050 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]2[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[S:12][CH:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:23](=[O:25])=[O:24].[OH-].[Na+]>O.CCOCC>[S:12]1[CH:13]=[C:9]([CH:8]=[CH:7][C:5]2[S:6][C:2]([C:23]([OH:25])=[O:24])=[CH:3][CH:4]=2)[C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]1=2

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 53963715HCID 53963715, compoundHCID 178418339Butyllithium

Product 1

HCID 53682346HCID 53682346, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred, chilled (-70° C.) solution of 3-[2-(5-bromo-2-thienyl)-ethenyl]benzo[b]thiophene (15.0 g) and ether (500 ml) was added n-butyl lithium (20.5 ml, 2.5M solution in hexanes) over 15 mins., under a nitrogen atmosphere. The mixture was stirred 1.5 hr, and was transferred under nitrogen to a vessel containing a large excess of dry ice and ether (500 ml). The suspension was stirred at room temperature overnight. The mixture was poured into water (1 L) and the mixture was basified with 2.5N sodium hydroxide solution. The organic phase was removed. The aqueous phase was acidified with 10% hydrochloric acid and extracted with dichloromethane. The combined, dried over anhydrous sodium sulfate, organic phase was concentrated, and the residue was recrystallized from toluene to give 7.10 g (52.8%) of product, mp 196°-197° C.

Workup

  1. customwas transferred under nitrogen to a vessel
  2. stirringThe suspension was stirred at room temperature overnight
  3. customThe organic phase was removed
  4. extractionextracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate, organic phase
  6. concentrationwas concentrated
  7. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-33621d7a7edf4c57a839757dc5798fee
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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