Hydrochloric Acid → HCID 11543982, compound

HRID 2243495Notes

Reaction equation

HRID 2243495 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[C:10]3[C:15]([CH:16]=[CH:17][C:7]=2[C:6]=1[O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].C1COCC1.O.[OH-].[Li+].Cl>O>[C:20]([CH2:19][O:18][C:6]1[C:7]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:8]=2[S:9][C:5]=1[C:3]([OH:4])=[O:2])([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68546537HCID 68546537, compound

Product 1

HCID 11543982HCID 11543982, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL round bottom flask added 3-ethoxycarbonylmethoxy-naphtho[1,2-b]thiophene-2-carboxylic acid methyl ester (0.116 g, 0.34 mmol) and 5 mL THF. To this mixture added a solution of lithium hydroxide hydrate (0.057 g, 1.35 mmol) in 3 mL water. This mixture was allowed to stir at room temperature for 16 hours. At this time 15 mL 1.2 N HCl was added, and a precipitate formed. The solids were collected by filtration and dried in vacuo. 3-carboxymethoxy-naphtho[1,2-b]thiophene-2-carboxylic acid was isolated as a tan solid (0.096 g, 93%). 1H NMR (400 MHz, DMSO-D6) δ ppm 5.06 (s, 2H) 7.69 (m, 2H) 7.91 (d, J=8.84 Hz, 1H) 7.95 (m, 1H) 8.08 (m, 1 H) 8.19 (t, J=4.0 Hz, 1H).

Workup

  1. customa precipitate formed
  2. filtrationThe solids were collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-27c1606a3fae4c4893e157503c4372b8
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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