Acetone → HCID 86706148, compound

HRID 2176300Notes

Reaction equation

HRID 2176300 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]([CH2:13][OH:14])([CH2:11][OH:12])[C:8](=[O:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([CH3:19])=O.COC(OC)(C)C>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:5][C:6]([C:7]1([C:8](=[O:10])[CH3:9])[CH2:11][O:12][C:17]([CH3:19])([CH3:16])[O:14][CH2:13]1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 180AcetoneHCID 64952,2-DimethoxypropaneHCID 85762566HCID 85762566, compound

Product 1

HCID 86706148HCID 86706148, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

A mixture of 2,2-bis-hydroxymethyl-3-oxo-butyric acid tert-butyl ester (8.67 g, 40 mmol), acetone (30 mL, 400 mmol), 2,2-dimethoxypropane (41.6 g, 50 mL, 400 mmol) and 4-toluenesulfonic acid hydrate (152 mg, 0.8 mmol) was stirred at room temperature for 18 h. The solvent was partially evaporated to a volume of ˜20 mL. Saturated sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic extracts were combined, washed with water and brine. The organic layer was filtered through a hydrophobic frit and the filtrate was evaporated. The residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 9:1 to 4:1 to afford the title compound (7.82 g, 75%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.39 (s, 3H), 1.44 (s, 3H), 1.48 (s, 9H), 2.32 (s, 3H), 6.36 (ABq, ΔδAB=0.05, JAB=11.8 Hz, 4H). LCMS (m/z) 281.2 [M+Na], Tr=2.44 min.

Workup

  1. customThe solvent was partially evaporated to a volume of ˜20 mL
  2. additionSaturated sodium hydrogen carbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with water and brine
  5. filtrationThe organic layer was filtered through a hydrophobic frit
  6. customthe filtrate was evaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c59890284e604b56b454fb7e354d0895
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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