HCID 74015247, compound → HCID 23072370, compound

HRID 1182453Notes

Reaction equation

HRID 1182453 reaction equation
[CH3:1][C:2]([CH3:21])([CH:10]([O:19][CH3:20])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH:3]=[CH:4][CH:5]=[CH:6][C:7]([OH:9])=[O:8]>CO.[Pd]>[CH3:1][C:2]([CH3:21])([CH:10]([O:19][CH3:20])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 74015247HCID 74015247, compound

Product 1

HCID 23072370HCID 23072370, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of carboxylic acid 25 (100 mg, 0.345 mmol) in MeOH (6 mL), at room temperature was added a solution of Pd/C 10% (50 mg, 1 mL in MeOH). The system was then purged with H2 several times to a final pressure of 50 psi. The reaction mixture was stirred for 3 h at room temperature, and then the solid was filtered through a Celite pad in a fritted glass funnel. The solvents were evaporated, and the crude material (100 mg, 99%) was pure enough for use in the next step: 1H NMR (300 MHz d6-acetone) δ 7.18 (d, J=8 Hz, 2H), 6.89 (d, J=8 Hz, 2H), 3.85 (s, 1H), 3.78 (s, 3H), 3.11 (s, 3H), 2.30 (br. t, J=7.5 Hz, 2H), 1.58-1.53 (m, 2H), 1.37-1.25 (m, 4H), 0.84 (s, 3H), 0.77 (s, 3H).

Workup

  1. customThe system was then purged with H2 several times to a final pressure of 50 psi
  2. filtrationthe solid was filtered through a Celite pad in a fritted glass funnel
  3. customThe solvents were evaporated

Sources & evidence

ORD record
ord-c6298a34fe874b5886d4c17afea3cbe9
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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