Dibenzyl ether → HCID 13027284, compound

HRID 1410652Notes

Reaction equation

HRID 1410652 reaction equation
[CH2:1]([O:8]CC1C=CC=CC=1)[C:2]1C=CC=C[CH:3]=1.[O:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>[Pd]>[O:16]1[CH2:21][CH2:20][O:19][CH:18]1[CH2:17][CH2:3][CH2:2][CH2:1][OH:8]

Participants

4

Reactant 2

HCID 7657Dibenzyl etherHCID 312751,4-Dioxane

Product 1

HCID 13027284HCID 13027284, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Benzyl ether of step 3 (2.00 g, 8.46 mmol, 1.0 equiv) was dissolved under argon in 1,4-dioxane (20 mL). Pd/C (10% Pd, 50 mg, 2.5 weight-%) was added. The mixture was purged with argon, and subsequently with hydrogen. The mixture was stirred at room temperature for 16 h. The solution was filtered (GF/A glass microfiber) and concentrated under reduced pressure to give the resulting alcohol (1.24 g, 8.46 mmol, 100%) as clear, colourless oil which was used in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ=4.86 (t, J=4.7 Hz, 1H), 4.00-3.91 (m, 2H), 3.90-3.80 (m, 2H), 3.65 (t, J=6.5 Hz, 2H), 1.74-1.66 (m, 2H), 1.66-1.58 (m, 2H), 1.56-1.46 (m, 2H), 1.40 (br s, 1H) ppm.

Workup

  1. customThe mixture was purged with argon
  2. filtrationThe solution was filtered (GF/A glass microfiber)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9e0444d6f3c48bda73ea38545f0ac8c
Source dataset
uspto-grants-2014_12
Patent number
US08921568B2

Reaction notes

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