Hydrochloric Acid → HCID 15062396, compound

HRID 1657199Notes

Reaction equation

HRID 1657199 reaction equation
CN(P(N(C)C)(N(C)C)=O)C.[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH:16]=[C:15]([CH3:20])[O:14]1.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Li+].CC([N-]C(C)C)C.Cl>C(OCC)(=O)C.CCOCC>[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH:16]=[C:15]([CH2:20][C:31](=[O:32])[CH2:30][O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:14]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 12679HexamethylphosphoramideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 177085Benzyloxyacetyl chlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 15062396HCID 15062396, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

In an argon gas stream, 13.75 ml of n-butyl lithium (1.6M solution in hexane) were added to 60 ml of an ether solution containing 2.35 g (0.022 mol) of diisopropylamine at -20° C. to form LDA. After stirring for 30 minutes, the solution was cooled to -78° C., and 6.93 ml (0.04 mol) of HMPA were added thereto, followed by stirring for 15 minutes. Afterward, a mixture of 2.84 g (0.02 mol) of 2,2-dimethyl-6-methyl-1,3-dioxin-4-one and 60 ml of ether as well as 60 ml of an ether solution containing 1.85 g (0.01 mol) of benzyloxyacetyl chloride were added to LDA. After the temperature was gradually returned to room temperature, 10% hydrochloric acid was added thereto to neutralize the solution, and extraction was then carried out with ether. The resultant organic layer was dried over anhydrous magnesium sulfate. Next, the used solvent was distilled off, and the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate =4:1), thereby obtaining 1.95 g (yield 67%) of 2,2-dimethyl-6-(3-benzyloxy-2-oxopropyl)-1,3-dioxin-4-one.

Workup

  1. stirringby stirring for 15 minutes
  2. customwas gradually returned to room temperature
  3. extractionthe solution, and extraction
  4. dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
  5. distillationNext, the used solvent was distilled off

Sources & evidence

ORD record
ord-f3eda8d8ab1942f0b821ae8a0450c1d7
Source dataset
uspto-grants-1993_10
Patent number
US05256800

Reaction notes

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