HCID 59350813, compound → HCID 59350800, compound

HRID 1644744Notes

Reaction equation

HRID 1644744 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:31])[CH:11]=2)[CH:6]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:31])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 59350813HCID 59350813, compound

Product 1

HCID 59350800HCID 59350800, compoundYield 120.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A round-bottom flask was charged with [4-(4-benzyloxy-benzyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (4.17 g, 9.73 mmol) in ethanol (250 mL). A full spatula scoop of 10% palladium on carbon was added into the reaction flask. The reaction mixture was stirred under hydrogen gas at atmospheric pressure overnight at room temperature. The reaction mixture was then filtered through a bed of celite. The filtrate was concentrated to afford 3.96 g (100%) of [6-fluoro-4-(4-hydroxy-benzyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester, which was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.17 (br. s, 1 H), 7.91 (dd, J=8.7, 6.2 Hz, 1 H), 7.74 (s, 1 H), 7.64 (dd, J=12.2, 1.9 Hz, 1 H), 7.33 (td, J=8.7, 1.9 Hz, 1 H), 6.83 (d, J=8.5 Hz, 2 H), 6.62 (d, J=8.5 Hz, 2 H), 4.32 (s, 2 H), 3.93 (s, 2 H), 3.64 (s, 3 H), 2.30 (s, 3 H).

Workup

  1. filtrationThe reaction mixture was then filtered through a bed of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2908862b254d4b549aad4a8ba165c036
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

Loading…