Lithium → HCID 22496314, compound

HRID 1015665Notes

Reaction equation

HRID 1015665 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[I:10])=[O:4].[Li]>O1CCOCC1.O>[I:10][C:9]1[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 20775765HCID 20775765, compound

Product 1

HCID 22496314HCID 22496314, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 3-Iodo-5-phenyl-thiophene-2-carboxylic acid methyl ester (4.4 g, 12.78 mmol) in dioxane/water 4/1 (50 ml), at 21° C., under N2, was treated with lithium hydroxyde (2N, 19.3 ml, 38 mmol) and the solution left to stir for 21.5 h. The reaction mixture was evaporated to dryness and the residue partitioned between EtOAc (75 ml) and water (25 ml) and acidified with 2N HCl to pH 5.5. The aqueous phase was separated and extracted with EtOAc (3×50 ml). The combined organic extract were washed with brine, dried and evaporated to give 4.12 g (97%) of 3-Iodo-5-phenyl-thiophene-2-carboxylic acid as a pale yellow solid. NMR 1H (CD3OD, 400 MHz): 7.69-7.67 (m, 2H); 7.55 (s, 1H); 7.46-7.39 (m, 3H).

Workup

  1. waitthe solution left
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue partitioned between EtOAc (75 ml) and water (25 ml)
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc (3×50 ml)
  6. extractionThe combined organic extract
  7. washwere washed with brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-9648f35ea4c945c885ca24b0dac25acf
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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