(+-)-2-Butanol → Sec-Butyl Propanoyloxymethyl Carbonate

HRID 1609747Notes

Reaction equation

HRID 1609747 reaction equation
[CH3:1][CH:2]([OH:5])[CH2:3][CH3:4].CN1CCOCC1.[C:13](Cl)(=[O:21])[O:14][CH2:15][O:16][C:17](=[O:20])[CH2:18][CH3:19]>C(Cl)(Cl)Cl>[C:13](=[O:21])([O:14][CH2:15][O:16][C:17](=[O:20])[CH2:18][CH3:19])[O:5][CH:2]([CH2:3][CH3:4])[CH3:1]

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 79724-MethylmorpholineHCID 14800977Propanoyloxymethyl Carbonochloridate

Product 1

HCID 20082466Sec-Butyl Propanoyloxymethyl CarbonateYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-butanol (0.92 mL, 10 mmol) and 4-methylmorpholine (1.1 mL, 10 mmol) in CHCl3 (20 mL) at -70° C. is added 7c (1.7 g, 10 mmol) during 20 min with stirring. The temperature is kept at -70° C. for 1 h and then raised (1 h) to room temperature. Next day following evaporation the residue is triturated with Et2O (25 mL) and filtered. The filtrate is evaporated and distilled to give 1.0 g (50%) of the title compound with bp 66°-68° C./5 mbar.

Workup

  1. customevaporation the residue
  2. customis triturated with Et2O (25 mL)
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. distillationdistilled

Sources & evidence

ORD record
ord-f63faf5d260844d8803fa6399414135a
Source dataset
uspto-grants-1995_03
Patent number
US05401868

Reaction notes

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