HCID 18008055, compound → HCID 18008100, compound

HRID 988246Notes

Reaction equation

HRID 988246 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:16]=[CH:17][CH:18]=1.[H][H]>CO.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 18008055HCID 18008055, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18008100HCID 18008100, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-[3-(naphthalen-2-ylmethoxy)-phenyl]-hex-5-ynoic acid (0.54 g, 1.4 mmol) in methanol (15 mL) is added 10% Pd/C (0.10 g) and this mixture is placed on a Parr apparatus and pressurized to 43 psi with hydrogen. This reaction is allowed to shake overnight. The reaction is filtered and the solvent removed in vacuo. The residue is purified by flash chromatography (silica, 5% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.83-7.89 (m, 4H), 7.46-7.56 (m, 3H), 7.17-7.22 (m, 1H), 6.77-6.85 (m, 3H), 5.21 (s, 2H), 2.59 (t, 2H), 2.31 (t, 2H), 1.58-1.70 (m, 6H); MS (EI) 348 (M)+.

Workup

  1. filtrationThe reaction is filtered
  2. customthe solvent removed in vacuo
  3. customThe residue is purified by flash chromatography (silica, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-98459ad27bbb46f5a24651bcf0532d3c
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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