Triethylamine hydrochloride → 5-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

HRID 1500148Notes

Reaction equation

HRID 1500148 reaction equation
COC([C:5]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]1=[O:12])=O.CN(C)C(=O)C.Cl.C(N(CC)CC)C.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH:5]2[C:6](=[O:12])[C:7]([CH3:11])([CH3:10])[CH2:8][CH2:9]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 31374DimethylacetamideHCID 11449298HCID 11449298, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 114248965-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

In 1-(4-chlorobenzyl)-3,3-dimethyl-2-oxocyclopentane carboxylic acid methyl ester (1.0 g, 0.00339 mol), N,N-dimethylacetamide (1 mL) and triethylamine hydrochloride (0.56 g, 0.00339×1.2 mol) were added and stirred at 150° C. for 2 hours. In the reaction liquid, toluene and saturated sodium bicarbonate water were added, and the mixture was partitioned. After extracting the aqueous layer using toluene, 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. additionwere added
  2. customthe mixture was partitioned
  3. extractionAfter extracting the aqueous layer
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThereafter, the dried
  7. customconcentrated product was purified
  8. customa target product was obtained

Sources & evidence

ORD record
ord-a77e6e71ec454d0ca4206654b4b546b0
Source dataset
uspto-grants-2015_12
Patent number
US09206106B2

Reaction notes

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