Ethanethiol → HCID 14307643, compound

HRID 868261Notes

Reaction equation

HRID 868261 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17](=[O:18])[CH:16]=[C:15]([CH2:19][CH2:20][CH3:21])[C:14](=[O:22])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[CH2:25]([SH:27])[CH3:26]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17](=[O:18])[C:16]([S:27][CH2:25][CH3:26])=[C:15]([CH2:19][CH2:20][CH3:21])[C:14](=[O:22])[C:11]=3[C:12]=2[CH3:13])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 14257811HCID 14257811, compound

Product 1

HCID 14307643HCID 14307643, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-(4-methoxybenzyl)-3-methyl-5-propyl-4,7-benzofurandione (from Example 28) (0.988 g, 3.05 mmol)in MeOH (23 mL) was added ethanethiol (2.5 mL). After a few minutes, the yellow quinone passed into solution giving a reddish colour. The reaction was cooled to 0° C. and solid FeCl3 (2.5 g) was added. The reaction was quenched 10% HCl and extraction with CH2Cl2 afforded the crude product which was chromatographed on silica gel (5% EtOAc/hexane) to yield the title compound.

Workup

  1. waitAfter a few minutes
  2. customgiving a reddish colour
  3. customThe reaction was quenched
  4. extraction10% HCl and extraction with CH2Cl2
  5. customafforded the crude product which
  6. customwas chromatographed on silica gel (5% EtOAc/hexane)

Sources & evidence

ORD record
ord-900ca7e0ef5d4fb19dc2fba4c504678f
Source dataset
uspto-grants-1988_10
Patent number
US04778805

Reaction notes

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