8-Hydroxyoctanoic acid → HCID 68194342, compound

HRID 876204Notes

Reaction equation

HRID 876204 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH3:12][O:13][C:14]1[CH:35]=[CH:34][C:17]([C:18](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:17]2[CH:34]=[CH:35][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 698208-Hydroxyoctanoic acidHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 68194342HCID 68194342, compoundYield 127.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-hydroxyoctanoic acid (100 mg, 0.59 mmol) was dissolved in 1.5 mL of pyridine. To the solution, 4,4′-dimethoxytrityl chloride (237 mg, 0.7 mmol) was added, and the mixture was stirred overnight. The completion of the reaction was confirmed by TLC. Then, the reaction solution was separated into organic and aqueous phases using methylene chloride and water. The organic phase was dried over sodium sulfate, and the solvent was then concentrated under reduced pressure. The residue was purified with a silica gel column (4 g, methylene chloride) to obtain amorphous 8-(4,4′-dimethoxytrityloxy)octanoic acid (348 mg). The obtained 8-(4,4′-dimethoxytrityloxy)octanoic acid was dissolved in 1 mL of methylene chloride. To the solution, 4-aminophenol (70.9 mg, 0.64 mmol), EDC (101.6 mg, 0.88 mmol), HOBT (79 mg, 0.886 mmol), and triethylamine (92 L) were added, and the mixture was stirred overnight. The completion of the reaction was confirmed by TLC. Then, the reaction solution was purified with a silica gel column (5 g, 30%-+50% ethyl acetate/n-hexane) to obtain the amorphous compound (148 mg).

Workup

  1. customThen, the reaction solution was separated into organic and aqueous phases
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationthe solvent was then concentrated under reduced pressure
  4. customThe residue was purified with a silica gel column (4 g, methylene chloride)

Sources & evidence

ORD record
ord-1fba6b51f64646a4a060fe1b991f7075
Source dataset
uspto-grants-2015_03
Patent number
US08987226B2

Reaction notes

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