Methanol → HCID 16103460, compound

HRID 1513843Notes

Reaction equation

HRID 1513843 reaction equation
[C:1]([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][CH2:29]CCCCCCC)=[C:18]([C:37]([O:39]CC)=[O:38])[S:17][C:16]=4[C:10]=3[S:9][C:8]=2[C:7]=1[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]CCCCCCC)([O:3]CC)=[O:2].CO.[OH-].[Li+]>O1CCCC1.O>[CH2:20]([C:19]1[C:15]2[S:14][C:11]3[C:12]4[S:13][C:6]([C:1]([OH:3])=[O:2])=[C:7]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:8]=4[S:9][C:10]=3[C:16]=2[S:17][C:18]=1[C:37]([OH:39])=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 887Methanol2×HCID 3939Lithium HydroxideHCID 67006721HCID 67006721, compound2×

Product 1

HCID 16103460HCID 16103460, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

Ester deprotection (Step C) The 2,6,-dicarboethoxy-3,7-diheptadecylthieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (5.00 g, 7.39 mmol) product of Example 6, was dissolved in tetrahydrofuran (THF) (280 mL) then methanol (40 mL) was added. Lithium hydroxide (707 mg, 29.5 mmol) was dissolved in water (7 mL) and added to the stirred methanol and THF solution. A condenser was fitted and the reaction mixture was heated in an oil bath at 90° C. for 16 hr. The THF and methanol were removed under reduced pressure. 60 mL of methanol and 10 mL of conc. hydrochloric acid were added then stirred for 4 h. Next 50 mL of water was added and the solid was filtered off. The product was dried under vacuum to give the 3,7-didecanyl thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene-2,6-dicarboxylic acid (4.50 g, 98% yield). 1H NMR (D8-THF)(of the di-lithium salt) δ 0.88 (6H, t, J=6.9 Hz), 1.20-1.47 (28H, m), 1.70-1.86 (4H, m), and 3.24 (4H, t, J=7.5 Hz).

Workup

  1. customA condenser was fitted
  2. customThe THF and methanol were removed under reduced pressure
  3. addition60 mL of methanol and 10 mL of conc. hydrochloric acid were added
  4. additionNext 50 mL of water was added
  5. filtrationthe solid was filtered off
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-a0efd2365d5d48b483405751b885ee82
Source dataset
uspto-grants-2012_07
Patent number
US08217183B2

Reaction notes

Loading…