Ethanol → 3,3-DIETHOXY-2-BUTANONE

HRID 1248660Notes

Reaction equation

HRID 1248660 reaction equation
Br[CH2:2][CH:3]1[CH:7]([CH2:8]Br)[O:6][C:5](=O)[O:4]1.N12CCCNC1C=CCC[CH2:12]2.[CH2:22]([OH:24])[CH3:23].C(OCC)C.CCCCCC>C(Cl)Cl>[CH2:7]([O:6][C:5]([O:4][CH2:3][CH3:2])([CH3:12])[C:22](=[O:24])[CH3:23])[CH3:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 150726561,2,3,4,6,7,8,10A-octahydropyrimido[1,2-a]azepineHCID 21584099Diethylether hexaneHCID 572608224,5-Bis(bromomethyl)-1,3-dioxolan-2-one

Product 1

HCID 109098623,3-DIETHOXY-2-BUTANONEYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 4,5-dibromomethyl-1,3-dioxolan-2-one (2.07 g, 7.6 mmole) and 1,8-diazabicyclo[5.4.0]undec-5-ene (2.26 ml, 15.2 mmole) in CH2Cl2 (20 ml) was stirred at 20° C. for 5 h, then anhydrous ethanol (5.0 ml, 85 mmole) was added, and the resulting mixture was stirred at 20° C. for 10 h. Flash chromatography (ethyl ether-hexane eluent) of the reaction mixture yielded 3,3-diethoxy-2-butanone as a colorless liquid (110 mg, 10%): IR (AgCl) 2965, 1722, 1350, 1253, 1133, 1050, 954 cm-1 ; 'H NMR (CDCl3) 1.23 (m, 9 H), 2.28 (s, 3 H), 3.50(q, J=7.5 Hz, 4 H).

Workup

  1. stirringthe resulting mixture was stirred at 20° C. for 10 h

Sources & evidence

ORD record
ord-3e72d399c97e4be491cc367a1404cbef
Source dataset
uspto-grants-1985_06
Patent number
US04525540

Reaction notes

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