Triethylamine → HCID 74538749, compound

HRID 1500145Notes

Reaction equation

HRID 1500145 reaction equation
COC([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:9][CH2:8][C:7]2([CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]2)[C:6]1=[O:17])=O.C(N(CC)CC)C.Cl.C(N(CC)CC)C.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.CN(C)C(=O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH:5]2[CH2:9][CH2:8][C:7]3([CH2:10][O:11][C:12]([CH3:16])([CH3:15])[O:13][CH2:14]3)[C:6]2=[O:17])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 86585896Sodium bicarbonate waterHCID 90097014HCID 90097014, compound

Product 1

HCID 74538749HCID 74538749, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
155 °C

Procedure

In 2-(4-chlorobenzyl)-8,8-dimethyl-1-oxo-7,9-dioxaspiro[4.5]decane-2-carboxylic acid methyl ester (2.0 g, 0.00546 mol), N,N-dimethylacetamide (2 mL), triethylamine (0.20 mL, 0.00546×0.3 mol), and triethylamine hydrochloride (1.13 g, 0.0546×1.5 mol) were added and stirred at 155° C. for 1.5 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-020e8ed924944a05a35bbd7ba0a19c57
Source dataset
uspto-grants-2015_12
Patent number
US09206106B2

Reaction notes

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