Boron trifluoride etherate → 1,1,3,3-Tetraethoxy-2-methylpropane

HRID 436703Notes

Reaction equation

HRID 436703 reaction equation
C(O[CH:5]([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])(=O)C.[CH:12]([O:15][CH2:16][CH3:17])=[CH:13][CH3:14].[CH2:18]([OH:20])[CH3:19].C(OCC)(OCC)OCC.B(F)(F)F.CCOCC>CCOCC>[CH2:10]([O:9][CH:5]([O:6][CH2:7][CH3:8])[CH:13]([CH3:14])[CH:12]([O:20][CH2:18][CH3:19])[O:15][CH2:16][CH3:17])[CH3:11]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 86734813Ethyl propenyl ether ethanol

Product 1

HCID 827611,1,3,3-Tetraethoxy-2-methylpropaneYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

A solution of one equivalent of diethoxymethyl acetate and one equivalent of a ethyl propenyl ether/ethanol mixture is stirred at ambient temperature for 30 min. followed by the addition of 1.3 equivalents of triethyl orthoformate. After cooling to 5° C. 1.5 ml. of boron trifluoride etherate is added and the resulting exotherm (5° to 37° C.) is controlled with an ice bath. After stirring at ambient temperature overnight the yellow reaction solution is diluted with ether and washed with water, saturated aqueous sodium bicarbonate and again with water. Drying (MgSO4) followed by solvent removal afforded a 92% yield of oil which is shown by glc to be ~80% pure product, δ(TMS, CDCl3) 4.44 (d, 2H, CH--O); 3.3-4.0 (complex, 8H, ethyl methylene), ~2.1 (m, 1H, CH3 --CH), 1.1 (t, 12H, ethyl methyls), and 1.0 (d, 3H, CH3 --CH).

Workup

  1. customthe resulting exotherm (5° to 37° C.) is controlled with an ice bath
  2. washwashed with water, saturated aqueous sodium bicarbonate and again with water
  3. dry with materialDrying (MgSO4)
  4. customfollowed by solvent removal

Sources & evidence

ORD record
ord-79655d8bfeb14fdd9df2747599e97d50
Source dataset
uspto-grants-1977_06
Patent number
US04028084

Reaction notes

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