Methyl 3-mercaptopropionate → HCID 44336570, compound

HRID 358838Notes

Reaction equation

HRID 358838 reaction equation
Br[CH:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[C:8]2[C:7]([OH:18])=[CH:6][CH:5]=[CH:4][C:3]1=2.[SH:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]>ClCCl>[CH3:25][O:24][C:22]([CH2:21][CH2:20][S:19][CH:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[C:8]2[C:7]([OH:18])=[CH:6][CH:5]=[CH:4][C:3]1=2)=[O:23]

Participants

4

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 27650410-Bromo-1,8-dihydroxy-10H-anthracen-9-one

Product 1

HCID 44336570HCID 44336570, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-Bromo-1,8-dihydroxy-9-anthrone (122 mg) was dissolved in dichloromethane (8 ml) and then methyl 3-mercaptopropionate (0.05 ml) was added. The red-brown solution became yellow-green immediately after addition of the thiol. The solution was stirred at room temperature for 5 hours. Removal of the solvent and recrystallisation of the residue from hexane gave the product (107.5 mg, 78%) as yellow needles, melting point 92°-94° C. (with decomposition).

Workup

  1. customRemoval of the solvent and recrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-4864dfb0ad6e45c18a27873ab9c35d94
Source dataset
uspto-grants-1991_03
Patent number
US04997961

Reaction notes

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