HCID 18008055, compound → HCID 18008100, compound

HRID 2117199Notes

Reaction equation

HRID 2117199 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-1a5607db5b35443aa8a66906f63a0d41
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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