HCID 11174412, compound → (S)-5-(4-hydroxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one

HRID 459194Notes

Reaction equation

HRID 459194 reaction equation
C([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][C@@H:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]2=[O:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][C@@H:14]2[O:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]2=[O:21])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 11174412HCID 11174412, compound

Product 1

HCID 10130705(S)-5-(4-hydroxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-oneYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-5-(4-benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one (1.0 g, 3.2 mmol) was combined with 10% Pd/C (0.75 g) in EtOAc (40 mL) and purged with N2 then H2 and then stirred under a hydrogen balloon for 3 hours. Sodium sulfate was added, and the mixture was filtered through Celite. The solvent was removed in vacuo to afford the title compound (0.747 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.11 (d, 2H, J=8.31 Hz), 6.76 (d, 2H, J=8.31 Hz), 4.93 (bs, 1H), 4.61 (dd, 1H, J=6.36 Hz, J=4.40 Hz), 3.11 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 2.98 (dd, 1H, J=14.67 Hz, J=5.86 Hz), 1.49 (s, 3H), 1.36 (s, 3H). MS (ES−) m/z mass calc'd for C12H14O4 (M−1) 221. Found m/z 221.

Workup

  1. custompurged with N2
  2. additionSodium sulfate was added
  3. filtrationthe mixture was filtered through Celite
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a56134324350465b8f8367c7518def68
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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