Hydrochloric Acid → HCID 11419622, compound

HRID 1373881Notes

Reaction equation

HRID 1373881 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])[CH:13]=2)[C:8]=1[Cl:32])C.[OH-].[K+].Cl>C1COCC1.O>[Cl:32][C:8]1[C:9]2[C:14](=[CH:13][C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:33])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69412293HCID 69412293, compound

Product 1

HCID 11419622HCID 11419622, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-chloro-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.0701 g, 0.146 mmol) and potassium hydroxide (0.032 g, 0.57 mmoles) in THF (4 mL) and water (4 mL) was stirred for 1.5 hours at ambient temperature. It was then poured in excess water and acidified with 2N hydrochloric acid. This was then extracted with ethyl acetate and washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, solvent evaporated dried in vacuo at 60° C. for 14 hours to yield [1-chloro-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid as a yellow semi-solid (0.0462 g, 69.9%); Mass spectrum (+ES, [M+H]+) m/z 453; 1H NMR (500 MHz, DMSO-d6): δ12.9–13.5 (br, 1H), 8.26 (d, 1H, J=8.85 Hz), 8.16 (d, 1H, J=1.83 Hz), 8.09–8.10 (m, 2H), 7.97–7.99 (m, 1H), 7.77 (dd, 1H, J=8.70 and 1.83 Hz), 7.47–7.56 (m, 3H), 5.03 (s, 2H), 2.43 (t, 2H, J=7.25 Hz), 1.42–1.48 (m, 2H), 0.98–1.06 (m, 2H), 0.59 ppm (t, 3H, J=7.40 Hz). Elemental Analysis for C25H21ClO4S+0.2 moles H2O: Calcd: C, 65.77; H, 4.72; N, 0.00; Found: C, 65.74; H, 4.99; N, 0.00.

Workup

  1. extractionThis was then extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customdried in vacuo at 60° C. for 14 hours

Sources & evidence

ORD record
ord-7cb381955d424d8490dd16f348e98685
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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