Dichloromethane → Ethyl (2R/S)-3-(3-bromo-1,4-naphthoquinon-2-yl)-2-methylpropionate

HRID 1527715Notes

Reaction equation

HRID 1527715 reaction equation
[Br:1][C:2]1[C:3]([CH2:16][CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([O:14]C)[C:5]2[C:10]([C:11]=1[O:12]C)=[CH:9][CH:8]=[CH:7][CH:6]=2.BrC1C(=O)C2C(=CC=CC=2)C(=O)C=1C(C)C(OCC)=O.C(Cl)Cl>CCCCCC>[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:14])[C:3]=1[CH2:16][CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70835186Ethyl (2R/S)-3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-2-methylpropionateHCID 86647738Ethyl (3-bromo-1,4-naphthoquinon-2-yl)-propionate

Product 1

HCID 70835151Ethyl (2R/S)-3-(3-bromo-1,4-naphthoquinon-2-yl)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Compound 68b was prepared from 67b (0.258 g, 0.678 mmol) as described above for 68a to give 0.064 g (0.18 mmol, 27%) of the product as a yellow solid following flash chromatography (3:1 CH2Cl2:hexane).

Sources & evidence

ORD record
ord-21c7d5fe473440338d8a0debf62076a8
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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