HCID 66900381, compound → HCID 66899808, compound

HRID 19397Notes

Reaction equation

HRID 19397 reaction equation
C([O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][C@H:14]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:19][C:16]1([CH3:20])[O:15][C@@H:14]([CH2:13][C:12]2[CH:21]=[CH:22][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:18][O:17]1

Participants

5

Reactant 2

HCID 66900381HCID 66900381, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66899808HCID 66899808, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-4-(4-benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolane (1.00 g, 3.35 mmol) in ethyl acetate (50 mL) was treated with 10% palladium on carbon (0.360 g, 0.34 mmol) and the resulting mixture hydrogenated under 1 atm of hydrogen pressure. The resulting mixture was filtered through a pad of Celite® and the pad of Celite washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol (696 mg, 100%).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. washthe pad of Celite washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2d0314668d2046899aac66a289043fb9
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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