Potassium Hydroxide → HCID 57900438, compound

HRID 1949955Notes

Reaction equation

HRID 1949955 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([O:17]C)=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+]>O1CCCC1.O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57900105methyl 8-bromo-4H-thieno[3,2-c]chromene-2-carboxylate

Product 1

HCID 57900438HCID 57900438, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a suspension of methyl 8-bromo-4H-thieno[3,2-c]chromene-2-carboxylate 2 (2.64 g, 8.12 mmol, 1 equiv) in 4:1 tetrahydrofuran/water (80 mL) was added aqueous potassium hydroxide (24 mL, 24 mmol, 3.0 equiv, 1.0 M solution in water) at 24° C. After 15 hr, the tetrahydrofuran was removed in vacuo (<20 mm Hg). The resulting aqueous suspension was diluted with water until all the solids were dissolved. To the resulting solution was added concentrated hydrochloric acid until the solution reached pH=1. The resulting solids were collected by filtration and dried in vacuo (<1 mm Hg) to afford 3bp as a yellow solid (2.36 g, 93%). 1H NMR (500 MHz, CDCl3), δ: 13.28 (br s, 1 H), 7.64 (d, J=2.4 Hz, 1 H), 7.60 (s, 1 H), 7.40 (dd, J=8.7, 2.4 Hz, 1 H), 6.94 (d, J=8.7 Hz, 1 H), 5.30 (s, 3 H).

Workup

  1. customthe tetrahydrofuran was removed in vacuo (<20 mm Hg)
  2. additionThe resulting aqueous suspension was diluted with water until all the solids
  3. dissolutionwere dissolved
  4. additionTo the resulting solution was added concentrated hydrochloric acid until the solution
  5. filtrationThe resulting solids were collected by filtration
  6. customdried in vacuo (<1 mm Hg)

Sources & evidence

ORD record
ord-10a80e03880541cc87226d70e7afecad
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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