Methane → HCID 20377694, compound

HRID 1703487Notes

Reaction equation

HRID 1703487 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([C:13]([C:15]3[CH:16]=[C:17]([CH:21]([CH2:26][CH2:27][CH2:28][CH3:29])[C:22]([O:24]C)=[O:23])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[CH:12][C:7]=2[CH:6]=1)=[O:4].C>[OH-].[K+]>[C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([C:13]([C:15]3[CH:16]=[C:17]([CH:21]([CH2:26][CH2:27][CH2:28][CH3:29])[C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[CH:12][C:7]=2[CH:6]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 20377690HCID 20377690, compound

Product 1

HCID 20377694HCID 20377694, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 2-{3-(5-methoxycarbonyl-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}hexanoate (29.6 g), suspended in a mixture of potassium hydroxide pellets (15.5 g), distilled water (50 cc) and ethanol (100 cc), is stirred for 17 hours at a temperature of about 20° C. The solvents are distilled off under reduced pressure (30 mm Hg) at 40°-50° C. and the residue is dissolved in distilled water (150 cc). The solution obtained is stirred with decolourizing charcoal (0.5 g), filtered and acidified to pH 1 by the addition of a 5N aqueous solution of hydrogen chloride. The resulting crystals are filtered off, washed three times with distilled water (total 150 cc) and dried under reduced pressure (20 mm Hg) at 70° C. in the presence of potassium hydroxide pellets. Crude 2-{3-(5-carboxy-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}hexanoic acid (28.4 g), melting at 208° C., is thus obtained.

Workup

  1. distillationdistilled water (50 cc) and ethanol (100 cc)
  2. distillationThe solvents are distilled off under reduced pressure (30 mm Hg) at 40°-50° C.
  3. dissolutionthe residue is dissolved in distilled water (150 cc)
  4. customThe solution obtained
  5. filtrationfiltered
  6. additionacidified to pH 1 by the addition of a 5N aqueous solution of hydrogen chloride
  7. filtrationThe resulting crystals are filtered off
  8. washwashed three times with distilled water (total 150 cc)
  9. dry with materialdried under reduced pressure (20 mm Hg) at 70° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-f84abdd2e6e9428680afcc705beda033
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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