9-Phenanthrol → Ethyl 2-hydroxy-2-(10-hydroxyphenanthren-9-yl)acetate

HRID 926192Notes

Reaction equation

HRID 926192 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[C:7]([CH:13]([OH:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]([CH3:20])=[CH:5]2.[CH:21]1[C:34]2C=C(O)C3C(=CC=CC=3)C=2C=C[CH:22]=1>>[OH:19][CH:13]([C:7]1[C:6]2[C:5]([C:4]3[CH:3]=[CH:2][CH:11]=[CH:10][C:9]=3[C:8]=1[OH:12])=[CH:34][CH:21]=[CH:22][CH:20]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 102299-PhenanthrolHCID 89676681Ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 89676749Ethyl 2-hydroxy-2-(10-hydroxyphenanthren-9-yl)acetate

Procedure

Prepared by the similar method to make ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate in Example 20, using phenanthren-9-ol instead of 6-bromo-3-methylnaphthalen-1-ol. 1H-NMR: 400 MHz, (CDCl3) δ: 8.90 (s, 1H), 8.66-8.62 (m, 2H), 8.40 (d, J=4.2 Hz, 1H), 7.97-7.94 (m, 1H), 7.71-7.49 (m, 4H), 6.23 (s, 1H), 4.14-4.08 (m, 2H), 3.81 (bs, 1H), 1.11 (t, J=7.4 Hz, 3H).

Workup

  1. customPrepared by the similar method

Sources & evidence

ORD record
ord-e62668537f5b4d1e9489827719a3a341
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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