HCID 10878747, compound → (+)-Solketal

HRID 1955359Notes

Reaction equation

HRID 1955359 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11]1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[CH3:15][C:12]1([CH3:16])[O:11][C@@H:10]([CH2:9][OH:8])[CH2:14][O:13]1

Participants

4

Reactant 1

HCID 10878747HCID 10878747, compound

Product 1

HCID 736057(+)-SolketalYield 87%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

10% Palladium-carbon (3 g) was added to thus obtained (S)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (16.692 g, 74.88 mmol) in ethanol(250 ml) and the mixture was stirred for 3 hours at 25° C. under an atmosphere of hydrogen. After the reaction was over, palladium-carbon was filtered off and the solution was condensed in vacuo. The crude product was distilled to give 8.61 g of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol (yield 87%, b.p. 65° C. at 3 mmHg, optical purity 97.8% e.e., specific rotation [α]D20 +10.92°(c=1,MeOH))).

Workup

  1. filtrationwas filtered off
  2. customcondensed in vacuo
  3. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-7cc8b28ff5c54c0499eb7681385d0289
Source dataset
uspto-grants-2000_09
Patent number
US06124479

Reaction notes

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