Hydrochloric Acid → HCID 178473090, compound

HRID 2216507Notes

Reaction equation

HRID 2216507 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3].[H-].[Na+].[C:20](OCC)(=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>CN(C=O)C>[OH:26]/[C:20](=[CH:1]\[C:2](=[O:3])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)/[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 178473090HCID 178473090, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxyacetophenone 1.1 (20.0 g, 88.4 mmol) in DMF (100 ml) at rt, was added NaH (60% in oil, 4.26 g, 106 mmol). The mixture was stirred at rt for 45 min, cooled to 0° C., and diethyl oxalate (14.4 ml, 106 mmol) was added dropwise, and the suspension warmed to rt and stirred for 17 h. The reaction mixture was poured over a mixture of ice and 1N HCl and the suspension stirred for 30 min, filtered, and the solid rinsed with water and dried to afford 28.9 g of the butenoate 1.2. MS (ESI) 325.2 (MH+).

Workup

  1. temperaturecooled to 0° C.
  2. temperaturethe suspension warmed to rt
  3. stirringstirred for 17 h
  4. stirringthe suspension stirred for 30 min
  5. filtrationfiltered
  6. washthe solid rinsed with water
  7. customdried

Sources & evidence

ORD record
ord-95c3b58d825c44b68d431c5af9c222ba
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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