2-(1-Benzyloxy-naphthalen-2-yl)benzoxazole-4-carboxylic acid methyl ester → 2-(1-Hydroxy-naphthalen-2-yl)benzoxazole-4-carboxylic acid methyl ester

HRID 70011Notes

Reaction equation

HRID 70011 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[O:13][C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[O:24]CC3C=CC=CC=3)=[N:11][C:10]=12)=[O:4]>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[O:13][C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[OH:24])=[N:11][C:10]=12)=[O:4]

Participants

4

Reactant 1

HCID 681624012-(1-Benzyloxy-naphthalen-2-yl)benzoxazole-4-carboxylic acid methyl ester

Product 1

HCID 1362241992-(1-Hydroxy-naphthalen-2-yl)benzoxazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(1-benzyloxy-naphthalen-2-yl)benzoxazole-4-carboxylic acid methyl ester, EtOAc (15.4 mL). 10% Pd/C (0.041 g, 0.376 mmol), 0.5 psi of H2(g) was consumed. Yield: 0.059 g of orange-yellow solid (75%). m.p. −185-186.5° C.; 1H NMR (400 MHz, CDCl3) δ 4.10 (s, 3H), δ 7.42-7.46 (m, 2H), δ 7.57-7.62 (m, 2H), δ 7.82 (d, J=8.3 Hz, 2H), δ 8.00 (d, J=8.7 Hz, 1H), δ 8.08 (dd, J=7.8 Hz, 1 Hz, 1H), δ 8.52 (d, J=8.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 52.45, 103.11, 114.83, 119.42, 120.95, 122.10, 123.93, 124.38, 126.05, 127.40, 127.68, 129.06; Anal. calcd for C19H13NO3 C, 71.47; H, 4.10; N, 4.39. Found C, 71.40; H, 4.12; N, 4.29.

Sources & evidence

ORD record
ord-d0d781b529cf4d22896fae19e72d04fc
Source dataset
uspto-grants-2014_09
Patent number
US08822515B2

Reaction notes

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