HCID 15086661, compound → HCID 15086664, compound

HRID 2108266Notes

Reaction equation

HRID 2108266 reaction equation
[CH3:1][C@@H:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29]CC4C=CC=CC=4)[C:24]=3[O:37]CC3C=CC=CC=3)[CH:12]=2)[CH:7]=1)[C:3]([OH:5])=[O:4].[H][H].OC1C(O)=CC=CC=1CCCCCCOC1C2C(=CC=CC=2)C=CC=1[C@H](C)C(O)=O>[Pd].C(OCC)(=O)C>[OH:37][C:24]1[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([C@H:2]([CH3:1])[C:3]([OH:5])=[O:4])[CH:15]=[CH:14]2

Participants

6

Reactant 3

HCID 15086661HCID 15086661, compoundHCID 53670307HCID 53670307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15086664HCID 15086664, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.9 g (8.3 mmol) of (S)-alpha-methyl-6-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid and 0.5 g of 10% palladium on carbon in 100 mL of ethyl acetate was shaken in a hydrogen atmosphere for 22 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated at reduced pressure to an oil which was crystallized from ether-hexane to give 2.9 g (85% yield), mp 136°-139°, of (S)-[6-(2,3-dihydroxyphenyl)hexyloxy]-alpha-methyl-2-naphthaleneacetic acid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated at reduced pressure to an oil which
  3. customwas crystallized from ether-hexane
  4. customto give 2.9 g (85% yield), mp 136°-139°

Sources & evidence

ORD record
ord-6c2e48095401448d97862b763e4da687
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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