Lithium Hydroxide → HCID 16103460, compound

HRID 83965Notes

Reaction equation

HRID 83965 reaction equation
C([O:3][C:4]([C:6]1[S:13][C:12]2[C:11]3[S:14][C:15]4[C:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:18]([C:30]([O:32]CC)=[O:31])[S:17][C:16]=4[C:10]=3[S:9][C:8]=2[C:7]=1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:5])C.[Li+].[OH-].C1COCC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH2:20]([C:19]1[C:15]2[S:14][C:11]3[C:12]4[S:13][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:8]=4[S:9][C:10]=3[C:16]=2[S:17][C:18]=1[C:30]([OH:32])=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

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) is 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 is heated at reflux overnight and most of the solvent is evaporated. The residue is acidified with concentrated HCl (30 mL). The resultant solid is 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 is heated
  2. temperatureat reflux overnight and most of the solvent
  3. customis evaporated
  4. filtrationThe resultant solid is collected by filtration
  5. washwashed thoroughly with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-f0058e8e041c49768232c4fa11e82164
Source dataset
uspto-grants-2014_09
Patent number
US08846855B2

Reaction notes

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