Tetrahydrofuran → HCID 14597184, compound

HRID 2051449Notes

Reaction equation

HRID 2051449 reaction equation
[CH2:1]([O:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]CC3C=CC=CC=3)=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O1CCCC1>[Pd].CO>[CH2:1]([O:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 14597189HCID 14597189, compound

Product 1

HCID 14597184HCID 14597184, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.03 g (2.8 mmol) of VII-15, 0.1 g of 5% Pd-C, 15 ml of tetrahydrofuran and 5 ml cf methanol were mixed and the mixture was subjected to catalytic hydrogenation under normal pressure. When the hydrogen absorption reached 66 ml, the reaction was stopped and the catalyst was filtered away. The filtrate was concentrated and purified by column chromatography to obtain 0.76 g (98% yield) of (+)-4'-(1-octyloxyethyl)4-biphenylcarboxylic acid. [α]D25 =+67.5° (c=1, CHCl3), m.p.=139°-140° C.

Workup

  1. customWhen the hydrogen absorption
  2. filtrationthe catalyst was filtered away
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-c3fdc6c1fadf4a1eb5de9f7ad10a1ea9
Source dataset
uspto-grants-1991_05
Patent number
US05019298

Reaction notes

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