Lithium Hydroxide → HCID 16103460, compound

HRID 1367443Notes

Reaction equation

HRID 1367443 reaction equation
[CH2:1]([C:11]1[C:15]2[S:16][C:17]3[C:21]4[S:22][C:23]([C:35]([O:37]CC)=[O:36])=[C:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:20]=4[S:19][C:18]=3[C:14]=2[S:13][C:12]=1[C:40]([O:42]CC)=[O:41])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Li+].[OH-].C1COCC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH2:25]([C:24]1[C:20]2[S:19][C:18]3[C:14]4[S:13][C:12]([C:40]([OH:42])=[O:41])=[C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:15]=4[S:16][C:17]=3[C:21]=2[S:22][C:23]=1[C:35]([OH:37])=[O:36])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 16103489Diethyl 3,7-didecylthieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene 2,6-dicarboxylate

Product 1

HCID 16103460HCID 16103460, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Procedure

Compound 74 (14.0 g, 0.021 mol) was mixed with LiOH (1.24 g, in 15 mL water), THF (100 mL), MeOH (20 mL) and a catalytic amount of tetrabutylammonium iodide. This mixture was heated at reflux overnight and most of the solvent was evaporated. The residue was acidified with concentrated HCl (30 mL). The resultant solid was collected by filtration, washed thoroughly with water and vacuum dried to yield compound 75 (12.5 g, 97.4% yield). M.p. 315.6-318.5° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux overnight and most of the solvent
  3. customwas evaporated
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed thoroughly with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-4de00664ef464092916da4a973c87be8
Source dataset
uspto-grants-2011_02
Patent number
US07893191B2

Reaction notes

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