Acetic Anhydride → 1,3-Dipivaloyl-2-acetoxymethyl glycerol

HRID 483675Notes

Reaction equation

HRID 483675 reaction equation
[C:1]([O:7][CH2:8][CH:9]([CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])OCOC)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:22]([O:25][C:26](=[O:28])[CH3:27])(=[O:24])C.B(F)(F)F.CCOCC>C(Cl)Cl>[C:1]([O:7][CH2:8][CH:9]([CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[O:24][CH2:22][O:25][C:26](=[O:28])[CH3:27])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 109796251,3-Dipivaloyl-2-methoxymethyl glycerol

Product 1

HCID 110458291,3-Dipivaloyl-2-acetoxymethyl glycerol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

50 g of 1,3-dipivaloyl-2-methoxymethyl glycerol, 150 ml of methylene chloride, and 17 ml of acetic anhydride was cooled to about -5° C. Then 0.3 ml of boron trifluoride etherate was added and the mixture was stirred for an additional 1 hr at about 0° C. then allowed to warm to 25° C. over an additional 1.5 hr. After this period, 100 ml saturated aqueous Na2Cl3 was added to the mixture followed by 100 ml CH2Cl2. After vigorous stirring for 5 min, the organic layer was separated and washed once with 100 ml H2O, once with aqueous NaCl, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 1,3-dipivaloyl-2-acetoxymethyl glycerol as a faintly colored oil.

Workup

  1. temperatureto warm to 25° C. over an additional 1.5 hr
  2. waitAfter this period
  3. stirringAfter vigorous stirring for 5 min
  4. customthe organic layer was separated
  5. washwashed once with 100 ml H2O, once with aqueous NaCl
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbeb750e3a844d4aaa2776fe2a154fb8
Source dataset
uspto-grants-1993_07
Patent number
US05225590

Reaction notes

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