Toluene → HCID 57293177, compound

HRID 36827Notes

Reaction equation

HRID 36827 reaction equation
[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][C:5]([CH2:9][OH:10])([CH3:8])[CH2:4][O:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[CH2:29]([O:36][CH2:37][CH2:38]OS(C(F)(F)F)(=O)=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.ClCCl>[CH3:1][C:2]1([CH3:11])[O:3][CH2:4][C:5]([CH2:9][O:10][CH2:38][CH2:37][O:36][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([CH3:8])[CH2:6][O:7]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 3737095-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxaneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 111298052-(Benzyloxy)ethyl Trifluoromethanesulfonate

Product 1

HCID 57293177HCID 57293177, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 2,2-dimethyl-5-hydroxymethyl-5-methyl-1,3-dioxane (13.4 g, 0.084 mol) in 630 mL of anhydrous tetrahydrofuran was cooled to -20° C. under argon atmosphere. Then a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene (168 mL, 0.084 mol) was added and the mixture was stirred at -20° C. for 1 hr. The 2-benzyloxyethyltriflate (23.8 g, 0.084 mol) was added neat, keeping the temperature between -20° and -15° C. The resulting solution was stirred at this temperature for 1 hr, then gradually allowed to warm to 25° C. and stirred for 15 hrs. Dichloromethane (900 mL) was added and the solution was washed twice with 300 mL of water and once with 100 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and evaporation of the solvents under reduced pressure gave 2,2-dimethyl-5-benzyloxyethoxymethyl-5-methyl-1,3-dioxane (24.6 g, 0.084 mol, 100%) which was not purified.

Workup

  1. customthe temperature between -20° and -15° C
  2. stirringThe resulting solution was stirred at this temperature for 1 hr
  3. temperatureto warm to 25° C.
  4. stirringstirred for 15 hrs
  5. washthe solution was washed twice with 300 mL of water and once with 100 mL of saturated sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate and evaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-ce6759d5b59c49ff9fe8c980a9e44a64
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Reaction notes

Loading…