Triethylamine hydrochloride → 2866-68-4

HRID 1500149Notes

Reaction equation

HRID 1500149 reaction equation
COC([CH:5]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:6]1=[O:18])=O.CN(C)C(=O)C.Cl.C(N(CC)CC)C.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH:7]2[CH2:8][CH2:9][CH2:5][C:6]2=[O:18])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 31374DimethylacetamideHCID 15100939HCID 15100939, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 111383252866-68-4

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

In 3-(4-chlorobenzyl)-2-oxocyclopentane carboxylic acid methyl ester (1.0 g, 0.00375 mol), N,N-dimethylacetamide (1 mL) and triethylamine hydrochloride (0.774 g, 0.00375×1.5 mol) were added and stirred at 130° C. for 2 hours, and then at 140° C. for another 3 hours. In the reaction liquid, ethyl acetate and saturated sodium bicarbonate water were added, and the mixture was partitioned. After extracting the aqueous layer using ethyl acetate, the organic layer was dried using anhydrous sodium sulfate and concentrated. Thereafter, the dried and concentrated product was purified using a silica gel column, and a target product was obtained.

Workup

  1. waitat 140° C. for another 3 hours
  2. additionwere added
  3. customthe mixture was partitioned
  4. extractionAfter extracting the aqueous layer
  5. customthe organic layer was dried
  6. concentrationconcentrated
  7. customThereafter, the dried
  8. customconcentrated product was purified
  9. customa target product was obtained

Sources & evidence

ORD record
ord-4fd196e6f7204210b74c6370839edbe8
Source dataset
uspto-grants-2015_12
Patent number
US09206106B2

Reaction notes

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