Reaction #64084

ord-e524e68b961847e189e32cc1fcedfdbf

Reaction equation

C[C@@H]1O[C@H](C(Cl)(Cl)Cl)OC(=O)[C@H]1C
(2S, 5S,6S)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one
O=S(=O)(O)O
sulfuric acid
CC(C)O
2-propanol
→
CC(C)OC(=O)[C@H](C)[C@H](C)O
isopropyl (2R, 3S)-2-methyl-3-hydroxybutanoate

Reactants

C[C@@H]1O[C@H](C(Cl)(Cl)Cl)OC(=O)[C@H]1C
(2S, 5S,6S)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one
O=S(=O)(O)O
sulfuric acid
CC(C)O
2-propanol

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionether extraction
  2. 2
    DryingThe ether phase was dried over anhydrous sodium sulfate and ether
  3. 3
    workup.DISTILLATIONwas distilled off
  4. 4
    workup.DISTILLATIONby distilling the residue

Procedure

To 1.0 g of (2S, 5S,6S)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one produced by a procedure similar to Example 1-(7) were added 0.1 ml of concentrated sulfuric acid and 10 ml of 2-propanol, stirred at room temperature for one hour, and 20 ml of water was added to effect ether extraction. The ether phase was dried over anhydrous sodium sulfate and ether was distilled off followed by distilling the residue to obtain 0.4 g of isopropyl (2R, 3S)-2-methyl-3-hydroxybutanoate of the following formula. ##STR61## (2) Repeating the procedure of Example 5-(1) except that 2-propanol was replaced with 2-butanol, 0.5 g of 1-methylpropyl (2R, 3S)-2-methyl-3-hydroxybutanoate of the following formula was obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05411877uspto-grants-1995_05