tert-Butanol → 3-Oxo-3-(tetrahydro-pyran-4-yl)-propionic Acid Tert-butyl Ester

HRID 1697665Notes

Reaction equation

HRID 1697665 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].CC1(C)OC(=O)[CH:10]([C:14]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[C:9](=O)[O:8]1>C1(C)C=CC=CC=1>[C:1]([O:5][C:9](=[O:8])[CH2:10][C:14](=[O:15])[CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 667706362,2-Dimethyl-5-(tetrahydro-pyran-4-carbonyl)-[1,3]dioxane-4,6-dione

Product 1

HCID 231440503-Oxo-3-(tetrahydro-pyran-4-yl)-propionic Acid Tert-butyl EsterYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butanol (600 ul, 6 mmol) was added to a solution of 2,2-dimethyl-5-(tetrahydro-pyran-4-carbonyl)-[1,3]dioxane-4,6-dione (1.1 g, 4 mmol) in toluene (9.6 ml). The reaction mixture was heated under reflux conditions for 6 h and partitioned between ice water/brine 1/1 and iPrOAc. The layers were separated and the aqueous layer was extracted one more time with iPrOAc. The combined extracts were washed with ice water/brine 1/1, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give the title compound (891 mg, 3.9 mmol; 91%) as brown oil which was sufficiently pure to be used in the next reaction step. MS (EI): m/z=228 [M]+.

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 6 h
  2. custompartitioned between ice water/brine 1/1 and iPrOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted one more time with iPrOAc
  5. washThe combined extracts were washed with ice water/brine 1/1
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-45e6e9a16d3b4f2882d6e10224b215d5
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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