Water → HCID 86744432, compound

HRID 1111230Notes

Reaction equation

HRID 1111230 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:12])[C:5]([O:10][CH3:11])=[CH:6][C:7](=[O:9])[CH:8]=1.O.CCN(C(C)C)C(C)C.[SH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]>C(O)C.C1COCC1>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([OH:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[OH:12].[SH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 65143-Mercaptopropionic AcidHCID 682622,6-Dimethoxy-1,4-benzoquinoneHCID 81531Diisopropylethylamine

Product 1

HCID 86744432HCID 86744432, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dimethoxybenzoquinone (2.0 g) was dissolved in ethanol (95%, 22 ml), water (6 ml), THF (15 ml) and DIEA (1.55 g). 3-mercaptopropionic acid (0.64 g) in ethanol (10 ml) was added in a dropwise fashion within 20 minutes, with stirring and cooling in an ice bath. The reaction was then allowed to proceed at room temperature. After 1.5 hours the reaction medium changed to a deep reddish color. The mixture was filtered and the filtrate evaporated in vacuo to give a solid mixture. This solid mixture was eluted via a silical gel chromatographic column (silica gel 60, [230-400 mesh], Merck) by using CHCl3 /MeOH/AcOH (97:2:1) as the mobile phase. The purified product DMQ-MP was crystallized from ether in a 26.5% yield (0.53 g). Melting point: 113°-115° C. Anal. calcd. for C11H14SO6, C 48.16, H 5.16; Found C 48.16, H 5.17. FABMS (fast atom bombardment mass spectrometry) [M-H]- (Xe beam) 273.19.

Workup

  1. temperaturecooling in an ice bath
  2. customto proceed at room temperature
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. customto give a solid mixture
  6. washThis solid mixture was eluted via a silical gel chromatographic column (silica gel 60, [230-400 mesh], Merck)
  7. customThe purified product DMQ-MP was crystallized from ether in a 26.5% yield (0.53 g)

Sources & evidence

ORD record
ord-d264a4b8ce364c998253ee55ac74f6a8
Source dataset
uspto-grants-1990_12
Patent number
US04978783

Reaction notes

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