HCID 10878747, compound → (+)-Solketal

HRID 1955355Notes

Reaction equation

HRID 1955355 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(OCC)(=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 91%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

10% Palladium-carbon (2.7 g) was added to thus obtained (S)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (16.228 g, 73.02 mmol) in ethyl acetate(270 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 solvent was condensed in vacuo. The crude product was distilled to give 8.78 g of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol (yield 91%, b.p. 70° C. at 6 mmHg, optical purity 97.2% e.e., specific rotation [α]D20 +10.76°(c=1,MeOH))).

Workup

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

Sources & evidence

ORD record
ord-c00e3e307d15476db26bd4c37c893503
Source dataset
uspto-grants-2000_09
Patent number
US06124479

Reaction notes

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