Hydrochloric Acid → HCID 22010409, compound

HRID 322882Notes

Reaction equation

HRID 322882 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:22][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])(=[O:3])[CH3:2].[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]=O.[OH-].[Na+].Cl>C(O)C.O>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:7]([O:6][C:5]1[CH:22]=[C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[CH:24]=[CH:25][C:4]=1[C:1](=[O:3])/[CH:2]=[CH:39]/[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=1)[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 10503817HCID 10503817, compound

Product 1

HCID 22010409HCID 22010409, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of ethyl (RS)-4-[2-acetyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)-butanoate (0.5 g) in ethanol (5 mL) is treated with pyridine-2-carboxaldehyde (0.12 g) and aqueous sodium hydroxide solution (0.95 g; 33% w/w) and stirred at 25° C. for 90 minutes. The solution is diluted with water and then brought to pH 7 by treatment with hydrochloric acid (2 M), forming a yellow gum. This gum is extracted with ethyl acetate, and the extract is washed with water, dried and evaporated. The resulting residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (65:35 v/v), followed by trituration with pentane, to give (E)-(RS)-4-(2-methylphenyl)-4-[2-{3-(2-pyridyl) prop-2-enoyl}-5-(3-thienylmethoxy)phenoxy]butanoic acid (0.22 g) in the form of a yellow solid, m.p. 65-70° C. [NMR(CDCl3):- 2.1-2.9 (4H,m),2.4(3H,s),4.9(2H,q),5.6(1H,q), 6.2-7.6(12H),7.7(1H,d,J=16 Hz),7.8(1H,t), 8.0(1H,d,J=16 Hz),8.6(1H,d)].

Workup

  1. customforming a yellow gum
  2. extractionThis gum is extracted with ethyl acetate
  3. washthe extract is washed with water
  4. customdried
  5. customevaporated
  6. washeluting with a mixture of ethyl acetate and pentane (65:35 v/v)

Sources & evidence

ORD record
ord-9626a1e16b364d25ba57d48e93e2d6a1
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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